6-(hydroxymethyl)-2,3,3-trimethyl-3H-indole | 143445-59-4

• 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: 6-(hydroxymethyl)-2,3,3-trimethyl-3H-indole
• 英文别名: (2,3,3-trimethylindol-6-yl)methanol
• CAS: 143445-59-4
• 化学式: C₁₂H₁₅NO
• mdl: MFCD09030871
• 分子量: 189.257
• InChiKey: FEQPNZLDTDFOKF-UHFFFAOYSA-N

物化性质

• 沸点：
  321.6±42.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

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：

  6-(hydroxymethyl)-2,3,3-trimethyl-3H-indole 在 新戊醇 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 14.25h， 生成 1-[(1',3',3'-Trimethyl-6-nitrospiro[chromene-2,2'-indole]-6'-yl)methyl]pyrrole-2,5-dione
  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 6-(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。
• 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.
• Alkali-metal cation recognition induced isomerization of spirobenzopyrans and spironaphthoxazins possessing a crown ring as a recognition site: multifunctional artificial receptors
  作者：Masahiko Inouye、Masaru Ueno、Kikuo Tsuchiya、Naomi Nakayama、Takashi Konishi、Teijiro Kitao

  DOI：10.1021/jo00046a019

  日期：1992.9

  Spirobenzopyrans and spironaphthoxazins possessing a monoaza-crown ring were synthesized. Isomerization of these compounds to the open colored merocyanines was induced by recognition of alkali-metal cations and the selectivity of the coloration was found to be governed by several factors: (1) the size of the crown ring, (2) the position of recognition, (3) electric properties of both the complexed cations and the merocyanine dipoles, and (4) the length of the alkyl chains connecting the spirobenzopyran units and the crown units. The spirobenzopyrans represent rationally designed multifunctional artificial receptors for alkali-metal cations.
• 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.