8-(iodomethyl)spirobenzopyran | 849113-99-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 8-(iodomethyl)spirobenzopyran
• 英文别名: 8-(Iodomethyl)-1',3',3'-trimethyl-6-nitrospiro[chromene-2,2'-indole]
• CAS: 849113-99-1
• 化学式: C₂₀H₁₉IN₂O₃
• 分子量: 462.287
• InChiKey: HKFPEJUXSJSSDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  58.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-(iodomethyl)spirobenzopyran 在 sodium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 28.0h， 生成 2-[4,7-Bis(carboxymethyl)-10-[(1',3',3'-trimethyl-6-nitrospiro[chromene-2,2'-indole]-8-yl)methyl]-1,4,7,10-tetrazacyclododec-1-yl]acetic acid
  参考文献：
  名称：

  Photochromically-controlled, reversibly-activated MRI and optical contrast agent

  摘要：

  将螺吡喃基团与Gd-DO3A半部分结合的造影剂在黑暗中具有更高的弛豫率和荧光强度；在可见光照射后，弛豫率和荧光强度会降低。

  DOI：

  10.1039/b616991k
• 作为产物：
  描述：

  3-氯甲基-5-硝基水杨醛 在 sodium iodide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 4.0h， 生成 8-(iodomethyl)spirobenzopyran
  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。
• Highly Axial Magnetic Anisotropy in a N₃O₅Dysprosium(III) Coordination Environment Generated by a Merocyanine Ligand
  作者：Pramila Selvanathan、Gang Huang、Thierry Guizouarn、Thierry Roisnel、Guglielmo Fernandez-Garcia、Federico Totti、Boris Le Guennic、Guillaume Calvez、Kévin Bernot、Lucie Norel、Stéphane Rigaut

  DOI：10.1002/chem.201603439

  日期：2016.10.17

  A spiropyran‐based switchable ligand isomerizes upon reaction with lanthanide(III) precursors to generate complexes with an unusual N3O5 coordination sphere. The air‐stable dysprosium(III) complex shows a hysteresis loop at 2 K and a very strong axial magnetic anisotropy generated by the merocyanine phenolate donor.

  基于螺吡喃的可转换配体在与镧系元素（III）前体反应后异构化，生成具有异常N 3 O 5配位球的复合物。空气稳定的complex（III）络合物在2 K处显示磁滞回线，并且由花青酚盐供体产生非常强的轴向磁各向异性。