2-(2-hydroxyethyl)-2-devinylchlorin e6 trimethyl ester | 73347-54-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: 2-(2-hydroxyethyl)-2-devinylchlorin e6 trimethyl ester
• CAS: 73347-54-3
• 化学式: C₃₇H₄₄N₄O₇
• 分子量: 656.779
• InChiKey: RBOGIUDTTMYENQ-TTXINOGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.15
• 重原子数：
  48.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  156.49
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-(2-hydroxyethyl)-2-devinylchlorin e6 trimethyl ester 在 sodium hydroxide 、 氯化亚砜 、 硫酸 、 potassium tert-butylate 、 氢溴酸 、 copper diacetate 、 potassium carbonate 、 叔丁醇 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.75h， 生成 δ-Methyl-2-(1-hydroxyethyl)-2-devinylpyropheophorbide a Methyl Ester
  参考文献：
  名称：

  Partial syntheses of optically pure methyl bacteriopheophorbides c and d from methyl pheophorbide a

  摘要：

  DOI：

  10.1021/jo01299a036
• 作为产物：
  描述：

  pheophorbide-a 在 硫酸 作用下， 生成 2-(2-hydroxyethyl)-2-devinylchlorin e6 trimethyl ester
  参考文献：
  名称：

  Synthesis, physicochemical properties and photocytotoxicity of five new δ-substituted chlorin e6 derivatives

  摘要：

  DOI：

  10.1016/s0040-4020(01)87917-5

文献信息

• Vinyl group protection in porphyrins and chlorins: Organoselenium derivatives
  作者：Sarah E. Brantley、Benjamin Gerlach、Marilyn M. Olmstead、Kevin M. Smith

  DOI：10.1016/s0040-4039(97)00002-6

  日期：1997.2

  The o-nitrophenylselenoethyl functionality is a useful protected vinyl group in porphyrins and chlorins, and its use is demonstrated in the Vilsmeier formylation reaction which has been shown to adversely affect unmodified vinyl groups in tetrapyrrole systems. The X-ray crystal structure for 3-(2-o-nitrophenylselenoethyl)-3-devinylchlorin-e(6) trimethyl ester 14 is reported. (C) 1997, Elsevier Science Ltd.
• Novel Synthetic Routes to 8-Vinyl Chlorophyll Derivatives
  作者：Benjamin Gerlach、Sarah E. Brantley、Kevin M. Smith

  DOI：10.1021/jo9721608

  日期：1998.4.1

  New methodology was developed toward the synthesis of 8-de-ethyl-8-vinylchlorophyll-a 1. Such 8-de-ethyl-8-vinyl derivatives of the green plant pigment chlorophyll-a 2 have been proposed to be intermediates during biosynthesis of chlorophylls and bacteriochlorophylls. Transformation of the 8-ethyl group to an 8-vinyl group was studied on derivatives (e.g. 5) of chlorin-e(6) trimethyl ester 9. The reported methodology involves regioselective osmylation on ring-B, followed by dehydration of the resulting 7,8-diol (e.g. 7). Based on a model synthesis, three partial synthetic approaches starting from 2 have been developed, using different protective groups for the 3-vinyl group. Several 8-de-ethyl-8-vinyl derivatives of 9 (e.g. 8 and its C-13-labeled analogue 22) have been synthesized. A new, mild recyclization method for fabrication of the isocyclic ring-E in chlorophylls was discovered which permits conversion of 8-de-ethyl-8-vinylchlorin-e(6) analogues 6 and 8 into the corresponding 8-de-ethyl-8-vinylpheophorbides 10 and 11. A change from vinyl to ethyl at the 3-position in chlorophylls causes a hypsochromic shift of 10 nm or more in the optical spectrum, whereas the identity of the 8-substituent (ethyl or vinyl) appears not to affect the wavelength of the band at about 660 nm. Hence, transformation from 8-vinyl to 8-ethyl during chloroplast biogenesis is a step which does not affect the light absorption/harvesting properties of the final isolated chlorophyll chromophores.