(all-E)-(7-formyl-2-methyl-2,4,6-octatrienyl)triphenylphosphonium chloride | 76686-48-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (all-E)-(7-formyl-2-methyl-2,4,6-octatrienyl)triphenylphosphonium chloride
• 英文别名: all-trans-(7-Formyl-2-methyl-2,4,6-octatrienyl)triphenylphosphoniumchlorid；(all-E)-(7-fomyl-2-methyl-2,4,6-octatrienyl)triphenylphosphonium chloride；[(2E,4E,6E)-2,7-dimethyl-8-oxoocta-2,4,6-trienyl]-triphenylphosphanium;chloride
• CAS: 76686-48-1
• 化学式: C₂₈H₂₈OP*Cl
• 分子量: 446.956
• InChiKey: YVWPVOVRIICKPU-UDSQFUDPSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (all-E)-(7-formyl-2-methyl-2,4,6-octatrienyl)triphenylphosphonium chloride 在 吡啶 、 Orthoameisensaeure-trimethylester 、 sodium ethanolate 、 对甲苯磺酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 43.5h， 生成 (3S,3'S)-7,8-二去氢虾青素
  参考文献：
  名称：

  合成胡萝卜素，天然胡萝卜素和天然维生素。八。合成冯（3小号，3'小号）-7,8,7'，8'- Tetradehydroastaxanthin UND（3小号，3'小号）-7,8- Didehydroastaxanthin（Asterinsäure）†往最‡

  摘要：

  光学活性天然类胡萝卜素和结构相关化合物的合成。八。（3 S，3 'S）-7,8,7'，8'-四氢紫黄嘌呤和（3 S，3 'S）-7,8-二氢紫黄嘌呤（Asterinic Acid）的合成

  DOI：

  10.1002/hlca.19800630618
• 作为产物：
  描述：

  (all-E)-8-hydroxy-2,7-dimethylocta-2,4,6-trienal 在 盐酸 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 18.67h， 生成 (all-E)-(7-formyl-2-methyl-2,4,6-octatrienyl)triphenylphosphonium chloride
  参考文献：
  名称：

  合成胡萝卜素，天然胡萝卜素和天然维生素。八。合成冯（3小号，3'小号）-7,8,7'，8'- Tetradehydroastaxanthin UND（3小号，3'小号）-7,8- Didehydroastaxanthin（Asterinsäure）†往最‡

  摘要：

  光学活性天然类胡萝卜素和结构相关化合物的合成。八。（3 S，3 'S）-7,8,7'，8'-四氢紫黄嘌呤和（3 S，3 'S）-7,8-二氢紫黄嘌呤（Asterinic Acid）的合成

  DOI：

  10.1002/hlca.19800630618

文献信息

• Carotenoids and Related Polyenes, Part 12 First Total Synthesis and Absolute Configuration of 3'-Deoxycapsanthin and 3,4-Didehydroxy-3'-deoxycapsanthin
  作者：Yumiko Yamano、Mahankhali Venu Chary、Akimori Wada

  DOI：10.1248/cpb.58.1362

  日期：——

  The synthesis of 3'-deoxycapsanthin (1) and 3,4-didehydroxy-3'-deoxycapsanthin (2), carotenoids of paprika, has been achieved by employing Lewis acid-promoted regio- and stereoselective rearrangement of the C(15)-epoxy dienal 5a. The absolute stereochemistry of the newly formed C-5 chiral center of rearrangement product 6a was determined to be (R) from its alternative synthesis derived from (+)-(R)-camphonanic

  辣椒粉的类胡萝卜素3'-脱氧辣椒素（1）和3,4-didehydroxy-3'-脱氧辣椒素（2）的合成已通过路易斯酸促进C（15）-的区域和立体选择性重排而实现环氧二烯5a。从其衍生自（+）-（R）-松香酸（11）的替代合成中，确定了新形成的重排产物6a的C-5手性中心的绝对立体化学为（R）。
• Total synthesis of capsanthin and capsorubin using Lewis acid-promoted regio- and stereoselective rearrangement of tetrasubsutituted epoxides
  作者：Yumiko Yamano、Masayoshi Ito

  DOI：10.1039/b710386g

  日期：——

  The synthesis of capsanthin 1 and capsorubin 2 was accomplished via the C(15)-cyclopentyl ketone 6 prepared by Lewis acid-promoted regio- and stereoselective rearrangement of the epoxy dienal 5.

  辣椒红素1和辣椒红素2的合成是通过路易斯酸促进环氧二烯基5的区域和立体选择性重排制备的C（15）-环戊基酮6完成的。
• Process for Synthesis of (3R,3'R,6'R)-Lutein and its Stereoisomers
  申请人：Khachik Frederick

  公开号：US20090264681A1

  公开（公告）日：2009-10-22

  (3R,3′R,6′R)-Lutein and (3R,3′R)-zeaxanthin are two dietary carotenoids that are present in most fruits and vegetables commonly consumed in the US. These carotenoids accumulate in the human plasma, major organs, and ocular tissues. In the past decade, numerous epidemiological and experimental studies have shown that lutein and zeaxanthin play an important role in the prevention of age-related macular degeneration (AMD) that is the leading cause of blindness in the U.S. and Western World. The invention provides a process for the synthesis of (3R,3′R,6′R)-lutein and its stereoisomers from commercially available (rac)-α-ionone by a C 15 +C 10 +C 15 coupling strategy. In addition, the present invention also provides access to the precursors of optically active carotenoids with 3-hydroxy-ε-end group that are otherwise difficult to synthesize. The process developed for the synthesis of lutein and its stereoisomers is straightforward and has potential for commercialization.

  (3R,3′R,6′R)-叶黄素和(3R,3′R)-玉米黄质是两种膳食类胡萝卜素，广泛存在于美国常见的大多数水果和蔬菜中。这些类胡萝卜素在人类血浆、主要器官和眼部组织中积累。在过去的十年里，许多流行病学和实验研究表明，叶黄素和玉米黄质在预防年龄相关性黄斑变性（AMD）中起着重要作用，这是美国和西方世界导致失明的主要原因。本发明提供了一种从商业可获得的（rac）-α-离子酮通过C15+C10+C15偶联策略合成(3R,3′R,6′R)-叶黄素及其立体异构体的方法。此外，本发明还提供了一种获得具有3-羟基-ε-末端基团的光学活性类胡萝卜素前体的方法，否则这些类胡萝卜素前体很难合成。用于合成叶黄素及其立体异构体的方法是简单明了的，并具有商业化潜力。
• Carotenoids and related polyenes. Part 8.1 Total synthesis of optically active mytiloxanthin applying the stereoselective rearrangement of tetrasubstituted epoxideWe have employed the numbering system used in carotenoids.
  作者：Chisato Tode、Yumiko Yamano、Masayoshi Ito

  DOI：10.1039/b201228f

  日期：2002.6.27

  Biomimetic synthesis of mytiloxanthin 1 was accomplished with stereoselective rearrangement of the tetrasubstituted epoxide 5 as a key reaction. This is the first total synthesis of optically active all-E mytiloxanthin 1.

  仿生黄体素1的仿生合成是通过四取代的立体选择性重排完成的环氧化物 5作为关键反应。这是光学活性全E甲黄嘌呤1的第一个全合成。
• Carotenoids and related polyenes. Part 9.1 Total synthesis of thermozeaxanthin and thermocryptoxanthin and the stabilizing effect of thermozeaxanthin on liposomes
  作者：Yumiko Yamano、Yoshitsugu Sakai、Masayuki Hara、Masayoshi Ito

  DOI：10.1039/b204011p

  日期：2002.8.23

  Thermozeaxanthin and thermocryptoxanthin are efficiently synthesized via β-selective glucosidation of (3R)-3-hydroxy-β-ionone 7, and the stabilizing effects of zeaxanthin 5, its glucoside 3 and thermozeaxanthin-15 1a on liposomes are also examined.

  通过对 (3R)-3-hydroxy-β-ionone 7 的 β 选择性葡萄糖苷化，高效合成了热玉米黄质和热隐玉米黄质，并研究了玉米黄质 5、其葡萄糖苷 3 和热玉米黄质-15 1a 对脂质体的稳定作用。