4-(hydroxymethyl)-2,3,3-trimethyl-3H-indole | 849114-05-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-(hydroxymethyl)-2,3,3-trimethyl-3H-indole
• 英文别名: (2,3,3-trimethylindol-4-yl)methanol
• CAS: 849114-05-2
• 化学式: C₁₂H₁₅NO
• mdl: MFCD09030868
• 分子量: 189.257
• InChiKey: MZWDARBYZWWGTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(hydroxymethyl)-2,3,3-trimethyl-3H-indole 在 四溴化碳 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 0.25h， 生成 4'-(Bromomethyl)-1',3',3'-trimethyl-6-nitrospiro[chromene-2,2'-indole]
  参考文献：
  名称：

  Family of Site-Selective Molecular Optical Switches

  摘要：

  [GRAPHIVS]We describe the design, synthesis, and characterization of a family of thiol-reactive optical switches for labeling proteins and other biomolecules. Site-selective introduction of photochromic probes within biomolecules is being used as part of a new approach for optical control of biomolecular interactions and activities within cells. The thiol-reactive photochromic probes described in this report include a spironaplithoxazine and five spirobenzopyrans. The location of the thiol-reactive group on the spirobenzopyran is different for each probe; this feature can be used to control the geometry of the optical switch within a bioconjugate. The photochromes undergo rapid and reversible, optically driven transitions between a colorless spiro (SP) state and a brightly colored merocyanine (MC) state. The MC absorption of a spironaphthoxazine conjugate is red shifted by more than 100 nm compared to the equivalent spirobenzopyran, which may be exploited for the independent control of the MC to SP transition for up to two different spironaphthoxazine and spirobenzopyran conjugates within the same sample.

  DOI：

  10.1021/jo048207o
• 作为产物：
  描述：

  3-氨基苯甲醇 在 盐酸 、 硫酸 、 tin(ll) chloride 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 19.5h， 生成 4-(hydroxymethyl)-2,3,3-trimethyl-3H-indole
  参考文献：
  名称：

  Family of Site-Selective Molecular Optical Switches

  摘要：

  [GRAPHIVS]We describe the design, synthesis, and characterization of a family of thiol-reactive optical switches for labeling proteins and other biomolecules. Site-selective introduction of photochromic probes within biomolecules is being used as part of a new approach for optical control of biomolecular interactions and activities within cells. The thiol-reactive photochromic probes described in this report include a spironaplithoxazine and five spirobenzopyrans. The location of the thiol-reactive group on the spirobenzopyran is different for each probe; this feature can be used to control the geometry of the optical switch within a bioconjugate. The photochromes undergo rapid and reversible, optically driven transitions between a colorless spiro (SP) state and a brightly colored merocyanine (MC) state. The MC absorption of a spironaphthoxazine conjugate is red shifted by more than 100 nm compared to the equivalent spirobenzopyran, which may be exploited for the independent control of the MC to SP transition for up to two different spironaphthoxazine and spirobenzopyran conjugates within the same sample.

  DOI：

  10.1021/jo048207o

文献信息

• PHOTOCHROMIC PROBES
  申请人：MARRIOTT J. D. Gerard

  公开号：US20070195309A1

  公开（公告）日：2007-08-23

  The present invention provides photochromic compounds and derivatives thereof as shown in claim 1 and methods of use of these compounds and derivatives. The present invention also provides photochromic optical probes capable of undergoing light directed reversible transition between a first state and a second state. The invention also teaches methods of determining and controlling reversible optical biomolecular interactions, for example binding of calcium in a subject.

  本发明提供了如权利要求1所示的光致变色化合物及其衍生物，以及这些化合物和衍生物的使用方法。本发明还提供了能够在第一状态和第二状态之间进行光导向可逆转换的光致变色光学探针。该发明还教授了确定和控制可逆光学生物分子相互作用的方法，例如在受试者中钙结合的方法。
• Water-Soluble Py-BIPS Spiropyrans as Photoswitches for Biological Applications
  作者：Cem Özçoban、Thomas Halbritter、Sabrina Steinwand、Lisa-Marie Herzig、Jörg Kohl-Landgraf、Noushin Askari、Florian Groher、Boris Fürtig、Christian Richter、Harald Schwalbe、Beatrix Suess、Josef Wachtveitl、Alexander Heckel

  DOI：10.1021/acs.orglett.5b00397

  日期：2015.3.20

  The ultrafast photochemistry of a new spiropyran photoswitch (Py-BIPS) has been investigated, revealing many advantages in the application in water over the previously studied spiropyrans. Functionalized Py-BIPS derivatives are presented for the study of pH dependence, stability, toxicity, and the thermal and photochemical behavior on longer time scales in aqueous media using several spectroscopic

  已经对新型螺吡喃光电开关（Py-BIPS）的超快光化学进行了研究，与先前研究的螺吡喃相比，揭示了在水中应用的许多优势。提出了功能化的Py-BIPS衍生物，用于使用几种分光镜方法研究水性介质中pH依赖性，稳定性，毒性以及在较长时间尺度上的热和光化学行为。这些研究为将Py-BIPS衍生物作为生物分子的光开关配体的实际应用铺平了道路。
• Rational design, synthesis, and characterization of highly fluorescent optical switches for high-contrast optical lock-in detection (OLID) imaging microscopy in living cells
  作者：Chutima Petchprayoon、Yuling Yan、Shu Mao、Gerard Marriott

  DOI：10.1016/j.bmc.2010.07.015

  日期：2011.2

  control of cellular processes. These studies require microscope imaging techniques and associated optical probes that provide high-contrast and high-resolution images of specific proteins and their complexes. Auto-fluorescence however, can severely compromise image contrast and represents a fundamental limitation for imaging proteins within living cells. We have previously shown that optical switch probes and optical lock-in detection (OLID) image microscopy improve image contrast in high background environments. Here, we present the design, synthesis, and characterization of amino-reactive and cell permeable optical switches that integrate the highly fluorescent fluorophore, tetramethylrhodamine (TMR) and spironaphthoxazine (NISO), a highly efficient optical switch. The NISO moiety in TMR-NISO undergoes rapid and reversible, excited-state driven transitions between a colorless Spiro (SP)-state and a colored merocyanine (MC)-state in response to irradiation with 365 and >530 nm light. In the MC-state, the TMR (donor) emission is almost completely extinguished by Forster resonance energy transfer (FRET) to the MC probe (acceptor), whereas in the colorless SP-state, the quantum yield for TMR fluorescence is maximal. Irradiation of TMR-NISO with a defined sequence of 365 and 546 nm manipulates the levels of SP and MC with concomitant modulation of FRET efficiency and the TMR fluorescence signal. High fidelity optical switching of TMR fluorescence is shown for TMR-NISO probes in vitro and for membrane permeable TMR-NISO within living cells. (C) 2010 Elsevier Ltd. All rights reserved.
• Preparation of a conjugation-ready thiol responsive molecular switch
  作者：Brandon Tautges、Victor Or、Joel Garcia、Jared T. Shaw、Angelique Y. Louie

  DOI：10.1016/j.tetlet.2015.10.019

  日期：2015.11

  In this work we synthesize molecular switches that are responsive to cysteine, homocysteine, and glutathione; three redox systems that make up the majority of the body's antioxidant defenses. Synthesized spiropyran isomers with conjugation-ready linkages showed good selectivity of response to these major antioxidant thiols over nucleophilic amino acids; however the position of the linking group can affect selectivity and reversibility of the switching response. An isomer with selectivity for cysteine against GSH and Hcy was identified. (C) 2015 Elsevier Ltd. All rights reserved.
• Family of Site-Selective Molecular Optical Switches
  作者：Tomoyo Sakata、Yuling Yan、Gerard Marriott

  DOI：10.1021/jo048207o

  日期：2005.3.1

  [GRAPHIVS]We describe the design, synthesis, and characterization of a family of thiol-reactive optical switches for labeling proteins and other biomolecules. Site-selective introduction of photochromic probes within biomolecules is being used as part of a new approach for optical control of biomolecular interactions and activities within cells. The thiol-reactive photochromic probes described in this report include a spironaplithoxazine and five spirobenzopyrans. The location of the thiol-reactive group on the spirobenzopyran is different for each probe; this feature can be used to control the geometry of the optical switch within a bioconjugate. The photochromes undergo rapid and reversible, optically driven transitions between a colorless spiro (SP) state and a brightly colored merocyanine (MC) state. The MC absorption of a spironaphthoxazine conjugate is red shifted by more than 100 nm compared to the equivalent spirobenzopyran, which may be exploited for the independent control of the MC to SP transition for up to two different spironaphthoxazine and spirobenzopyran conjugates within the same sample.