rac-hept-1-ene-4,6-diyn-3-ol | 14304-31-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: rac-hept-1-ene-4,6-diyn-3-ol
• 英文别名: Hepta-1-en-4,6-diin-3-ol；hept-1-ene-4,6-diyn-3-ol；1-Hepten-4,6-diin-3-ol；1-Heptene-4,6-diyn-3-ol；hept-1-en-4,6-diyn-3-ol
• CAS: 14304-31-5
• 化学式: C₇H₆O
• 分子量: 106.124
• InChiKey: QDWDAWJYZMHUPK-UHFFFAOYSA-N

物化性质

• 沸点：
  178.6±33.0 °C(Predicted)
• 密度：
  1.019±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  rac-hept-1-ene-4,6-diyn-3-ol 在 4-二甲氨基吡啶 、 Candida antarctica B lipase 、 Na₂HPO₄ buffer 、 三乙胺 作用下， 反应 7.5h， 生成 (3S)-hept-1-ene-4,6-diyn-3-ol
  参考文献：
  名称：

  Chemoenzymatic Asymmetric Total Syntheses of Antitumor Agents (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and (R)- and (S)-Falcarinol from Panax ginseng Using an Enantioconvergent Enzyme-Triggered Cascade Reaction

  摘要：

  Total asymmetric synthesis of two components of Panax ginseng showing antitumor activity, i.e., (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and of both enantiomers of Falcarinol was accomplished. Due to the fact that the synthetic strategy was based on enantio-convergent biotransformations, the occurrence of any undesired stereoisomer was entirely avoided. The absolute configuration of naturally occurring Panaxytriol was confirmed to be (3R,9R,10R) on the basis of optical rotation values. It was shown that enzyme-triggered cascade reactions represent a valuable tool for the synthesis of natural products.

  DOI：

  10.1021/jo020073w
• 作为产物：
  描述：

  7-(trimethylsilyl)hept-1-ene-4,6-diyn-3-ol 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以0.92 g的产率得到rac-hept-1-ene-4,6-diyn-3-ol
  参考文献：
  名称：

  （+）和（-）-法卡林醇的简短合成

  摘要：

  报道了双炔天然产物falcarinol 1的短而实用的合成。该方法依赖于双-三甲基甲硅烷基丁二炔10的替代功能化。这可以在一锅中实现，但是，更常规地获得了更好的产量。脂肪酶介导的外消旋加合物在有机溶剂中的酶促动力学拆分，得到（+）- 1的对映体过量为97％。在水性条件下用外消旋的3-乙酰氧基福尔卡诺醇11进行的类似过程得到（-）- 1。用Dess-Martin高碘烷氧化1可以得到falcarinone 2。

  DOI：

  10.1016/j.tet.2010.10.049

文献信息

• Absolute Structure of Panaxytriol.
  作者：Mitsuru Satoh、Masayoshi Ishii、Mitsuo Watanabe、Kimiaki Isobe、Taketo Uchiyama、Yasuo Fujimoto

  DOI：10.1248/cpb.50.126

  日期：——

  Diastereomeric mixture at C-3 of (9R, 10R)-panaxytriol acetonide (3) and (9S, 10S)-panaxytriol acetonide (4) were enantioselectively acetylated to give (3R)-acetates (3a-Ac, 4a-Ac) and (3S)-alcohols (3b, 4b) by enzyme mediated-acetylation using CHIRAZYME and vinyl acetate, respectively. Hydrolysis of (3R)-acetate (3a-Ac, 4a-Ac) with CHIRAZYME and phosphate buffer afforded (3R)-alcohols (3a, 4a), respectively. Deprotection of panaxytriol acetonides (3a, 3b, 4a, 4b) gave panaxatriol and its isomers, respectively. Comparison of optical rotation values of the synthetic panaxatriols with that of the natural one confirmed that the absolute configuration of panaxytriol sould be 3R, 9R, 10R.

  通过使用 CHIRAZYME 和乙酸乙烯酯进行酶介导乙酰化，(9R, 10R)-panaxytriol acetonide (3) 和 (9S, 10S)-panaxytriol acetonide (4) C-3 处的非对映混合物被对映选择性乙酰化，分别得到 (3R)-acetates (3a-Ac, 4a-Ac) 和 (3S)-alcohols (3b, 4b)。用 CHIRAZYME 和磷酸盐缓冲液水解 (3R)-acetate (3a-Ac, 4a-Ac)，分别得到 (3R)-alcohols (3a, 4a)。对三羟甲基丙酮（3a、3b、4a、4b）进行脱保护处理后，分别得到三羟甲基丙酮及其异构体。通过比较合成的三七酚与天然三七酚的旋光度值，证实三七酚的绝对构型应为 3R、9R、10R。
• Total synthesis of the falcarinol-type oxylipin (3S)-16,17-didehydrofalcarinol and its activity against Leishmania mexicana
  作者：Horacio Larqué、Ana G. Carrillo-Aké、Jennifer de la Vega、Sergio R. Peraza-Sánchez、Rubén M. Carballo、Abelardo Chávez-Montes、Esther del Olmo

  DOI：10.1016/j.tet.2022.132832

  日期：2022.7

  This paper reports a novel synthesis route to obtain (3S)-16,17-didehydrofalcarinol (1a) in order to provide the quantities necessary for in vivo tests. For this purpose, a two-synthon coupling synthesis was applied. On the one hand, the (Z)-10-bromodeca-1,8-diene (10) was obtained throughout nine steps, and on the other, the hepta-1-en-4,6-diyn-3-ol (11) was obtained in one single step, the fragments

  本文报道了一种获得 (3 S )-16,17-二去氢法尔卡林醇 ( 1a ) 的新合成途径，以提供体内试验所需的数量。为此目的，应用了双合成子偶联合成。一方面，通过九步得到( Z )-10-bromodeca-1,8-diene ( 10 )，另一方面，hepta-1-en-4,6-diyn-3-ol ( 11 )在一个单一步骤中获得，片段被偶联得到外消旋1，产率为27%。最后，手性色谱分离1提供了所需的对映异构体1a (27 mg)，其针对墨西哥利什曼原虫进行了测试, 证明了其高效的生物活性 (IC 50  = 0.74 μM)。
• Synthesis of Ginseng Diyne Analogues and Their Antiproliferative Activity against L1210 Cells
  作者：Kim Shin-Il、Lee You-Hui、Ahn Byung-Zun

  DOI：10.1002/(sici)1521-4184(19994)332:4<133::aid-ardp133>3.0.co;2-g

  日期：1999.4

  Some analogues of Ginseng diyne were synthesized and tested for antiproliferative activity against L1210 cells. The epoxy moiety of panaxydol, isolated from the root of Panax ginseng, proved to be in the cis-form on comparison with synthetic specimens. Analysis of structure-activity relationship revealed that the presence of the heptadec-1-ene-4,6-diyn-3-ol moiety in the structure of the analogues was essential for their antiproliferative activity and that the epoxy and alkyl groups in the structure contributed to enhancement of the antiproliferative activity.
• Studies towards the Biomimetic Synthesis of Ginsenoyne L; Efficient Synthesis of 2'-epi-Ginsenoyne L
  作者：Jack E. Baldwin、Robert M. Adlington、Peter J. Wilkinson、Rodolfo Marquez、Mauro F. A. Adamo

  DOI：10.3987/com-02-s25

  日期：——
• Chemoenzymatic Asymmetric Total Syntheses of Antitumor Agents (3<i>R</i>,9<i>R</i>,10<i>R</i>)- and (3<i>S</i>,9<i>R</i>,10<i>R</i>)-Panaxytriol and (<i>R</i>)- and (<i>S</i>)-Falcarinol from <i>Panax </i><i>g</i><i>inseng</i> Using an Enantioconvergent Enzyme-Triggered Cascade Reaction
  作者：Sandra F. Mayer、Andreas Steinreiber、Romano V. A. Orru、Kurt Faber

  DOI：10.1021/jo020073w

  日期：2002.12.1

  Total asymmetric synthesis of two components of Panax ginseng showing antitumor activity, i.e., (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and of both enantiomers of Falcarinol was accomplished. Due to the fact that the synthetic strategy was based on enantio-convergent biotransformations, the occurrence of any undesired stereoisomer was entirely avoided. The absolute configuration of naturally occurring Panaxytriol was confirmed to be (3R,9R,10R) on the basis of optical rotation values. It was shown that enzyme-triggered cascade reactions represent a valuable tool for the synthesis of natural products.