(2'R,5'Z,4''E,8''E,12''E)-2-[5'-(4'',9'',13'',17''-tetramethyloctadeca-4'',8'',12'',16''-tetraenylidene)tetrahydropyran-2'-yl]prop-2-enoic acid | 183381-06-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2'R,5'Z,4''E,8''E,12''E)-2-[5'-(4'',9'',13'',17''-tetramethyloctadeca-4'',8'',12'',16''-tetraenylidene)tetrahydropyran-2'-yl]prop-2-enoic acid
• 英文别名: (+)-hippospongic acid A；hippospongic acid A；(R)-hippospongic acid A；2-[(2R)-5-[(4E,8E,12E)-4,9,13,17-Tetramethyl-4,8,12,16-octadecatetrene-1-ylidene]tetrahydro-2H-pyran-2-yl]propenoic acid；2-[(2R,5Z)-5-[(4E,8E,12E)-4,9,13,17-tetramethyloctadeca-4,8,12,16-tetraenylidene]oxan-2-yl]prop-2-enoic acid
• CAS: 183381-06-8
• 化学式: C₃₀H₄₆O₃
• 分子量: 454.693
• InChiKey: HJNULIFEXQNJKQ-WJJPFERQSA-N

物化性质

• 沸点：
  583.3±50.0 °C(Predicted)
• 密度：
  0.991±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2'R,5'Z,4''E,8''E,12''E)-2-[5'-(4'',9'',13'',17''-tetramethyloctadeca-4'',8'',12'',16''-tetraenylidene)tetrahydropyran-2'-yl]prop-2-enoic acid 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 生成 dodecahydrohippospongic acid A methyl ester
  参考文献：
  名称：

  Enantioselective total synthesis and absolute stereostructure of hippospongic acid A

  摘要：

  A compound having the structure proposed for hippospongic acid A, a triterpene that specifically inhibits gastrulation of starfish embryos, was synthesized enantioselectively. The synthetic compound was not identical to the natural product. Comparison of the NMR spectra of the natural and synthetic compounds led us to propose an alternative structure, which was confirmed by enantioselective synthesis. The present synthesis established that the natural product has the (R)-configuration. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01129-7
• 作为产物：
  描述：

  (2'R,5'Z,4''E,8''E,12''E)-2-[5'-(4'',9'',13'',17''-tetramethyloctadeca-4'',8'',12'',16''-tetraenylidene)tetrahydropyran-2'-yl]prop-2-en-1-ol 在 manganese(IV) oxide 、 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 作用下， 生成 (2'R,5'Z,4''E,8''E,12''E)-2-[5'-(4'',9'',13'',17''-tetramethyloctadeca-4'',8'',12'',16''-tetraenylidene)tetrahydropyran-2'-yl]prop-2-enoic acid
  参考文献：
  名称：

  修订的马六甲酸A的结构，合成和绝对构型

  摘要：

  对马六甲酸A的结构进行了重新研究，并获得了支持先前提出的修订结构的新证据。通过对映选择性合成建立了包括绝对构型在内的结构。

  DOI：

  10.1016/s0040-4039(98)01688-8

文献信息

• Development of Aliphatic Alcohols as Nucleophiles for Palladium-Catalyzed DYKAT Reactions:  Total Synthesis of (+)-Hippospongic Acid A
  作者：Barry M. Trost、Michelle R. Machacek、Hong C. Tsui

  DOI：10.1021/ja050340q

  日期：2005.5.1

  The ability to use aliphatic alcohols as competent nucleophiles in the palladium-catalyzed dynamic kinetic asymmetric transformation of Baylis-Hillman adducts is explored. High yield and enantioselectivity is obtained for both the kinetic transformation and dynamic kinetic transformation. The absolute stereochemistry of the products is used to explore the reactive conformation of 2-substituted pi-allyl

  探索了在钯催化的 Baylis-Hillman 加合物的动态动力学不对称转化中使用脂肪醇作为感受态亲核试剂的能力。动力学转化和动态动力学转化均获得高产率和对映选择性。产品的绝对立体化学用于探索 2-取代的 pi-烯丙基配合物与基于 DPPBA 的手性配体的反应构象。在原肠形成抑制剂 (+)-河马酸 A 的简明全合成的背景下进一步证明了该方法的实用性。该合成具有三个钯催化的烯丙基烷基化反应，以引入三种不同的键类型：CS、CH 和公司。
• Revised structure, synthesis and absolute configuration of hippospongic acid A
  作者：Hideaki Hioki、Masayo Hamano、Yumi Mimura、Mitsuaki Kodama、Shinji Ohta、Mihoko Yanai、Susumu Ikegami

  DOI：10.1016/s0040-4039(98)01688-8

  日期：1998.10

  The structure of hippospongic acid A was reinvestigated and new evidence supporting the revised structure previously proposed was obtained. The structure, including absolute configuration, was established by the enantioselective synthesis.

  对马六甲酸A的结构进行了重新研究，并获得了支持先前提出的修订结构的新证据。通过对映选择性合成建立了包括绝对构型在内的结构。
• Enantioselective total synthesis and absolute stereostructure of hippospongic acid A
  作者：Hideaki Hioki、Hidenori Ooi、Masayo Hamano、Yumi Mimura、Suzuyo Yoshio、Mitsuaki Kodama、Shinji Ohta、Mihoko Yanai、Susumu Ikegami

  DOI：10.1016/s0040-4020(00)01129-7

  日期：2001.2

  A compound having the structure proposed for hippospongic acid A, a triterpene that specifically inhibits gastrulation of starfish embryos, was synthesized enantioselectively. The synthetic compound was not identical to the natural product. Comparison of the NMR spectra of the natural and synthetic compounds led us to propose an alternative structure, which was confirmed by enantioselective synthesis. The present synthesis established that the natural product has the (R)-configuration. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of (R)-(+)-Hippospongic Acid A, a Triterpene Isolated from the Marine Sponge, Hippospongia sp.
  作者：Miwako ICHIHASHI、Hirosato TAKIKAWA、Kenji MORI

  DOI：10.1271/bbb.65.2569

  日期：2001.1

  Hippospongic acid A (1) is a triterpene metabolite of the marine sponge, Hippospongia sp., with inhibitory activity against the gastrulation of starfish embryos. (R)-(+)-1 was synthesized by employing enzymatic kinetic resolution as the key step.

  海马海绵酸 A (1) 是海洋海绵海马海绵的一种三萜类代谢物，对海星胚胎的胃形成具有抑制活性。(R)-(+)-1是通过酶动力学解析这一关键步骤合成的。