(S)-nonadec-1-en-4-ol | 528867-18-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-nonadec-1-en-4-ol
• 英文别名: (4S)-Nonadec-1-EN-4-OL；(4S)-nonadec-1-en-4-ol
• CAS: 528867-18-7
• 化学式: C₁₉H₃₈O
• 分子量: 282.51
• InChiKey: ZLGVCQXWYKJRPY-LJQANCHMSA-N

物化性质

• 沸点：
  376.7±11.0 °C(Predicted)
• 密度：
  0.842±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  20
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  (S)-nonadec-1-en-4-ol 在 咪唑 、 臭氧 、 (+)-二异松蒎基氯硼烷 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.5h， 生成 (4R,6S)-heneicos-1-ene-4,6-diol
  参考文献：
  名称：

  抗原选择性合成原虫内酯西番莲菌A及其七个异构体

  摘要：

  具有对原生动物活性的天然产物共轭的δ-内酯西番莲菌素A及其七个异构体以对映体纯的形式合成。已经表明以这种方式提出的天然化合物的结构是错误的。现在证明了正确的结构。合成的关键步骤是不对称的布朗型醛烯丙基化和闭环复分解。

  DOI：

  10.1021/jo049275d
• 作为产物：
  描述：

  乙酸烯丙酯 、 1-十六烷醇 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 caesium carbonate 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 、 4-氯-3-硝基苯甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以72%的产率得到(S)-nonadec-1-en-4-ol
  参考文献：
  名称：

  对映选择性铱催化的醇CH烯丙基化反应全合成隐烯丙酚A

  摘要：

  通过铱催化的对映选择性二醇双CHH烯丙基化反应可分8个步骤制备聚酮化合物天然产物隐香碳烯醇A，该化合物可直接生成基于乙酸盐的三酮化合物立体二胺。在先前报告的4个总合成中，需要17-28个步骤。

  DOI：

  10.1002/anie.201600591

文献信息

• On the Structure of Passifloricin A:  Asymmetric Synthesis of the δ-Lactones of (2<i>Z</i>,5<i>S</i>,7<i>R</i>,9<i>S</i>,11<i>S</i>)- and (2<i>Z</i>,5<i>R</i>,7<i>R</i>,9<i>S</i>,11<i>S</i>)-Tetrahydroxyhexacos-2-enoic Acid
  作者：Jorge García-Fortanet、Juan Murga、Miguel Carda、J. Alberto Marco

  DOI：10.1021/ol034182o

  日期：2003.5.1

  graphicStereoselective syntheses of the delta-lactone of (2Z,5S,7R,9S,11S)-tetrahydroxyhexacos-2-enoic acid, the structure reported for passifloricin A, and of its (5R)-epimer are described. The creation of all stereogenic centers relied upon Brown's asymmetric allylation methodology. The lactone ring was created via ring-closing metathesis. The NMR data of both synthetic products, however, were different from those of the natural product. The published structure of passifloricin A is thus erroneous and will require further synthetic work to be unambiguously assigned.
• Enantioselective allyltitanations: synthesis of the proposed structures for passifloricin A
  作者：Samir BouzBouz、Janine Cossy

  DOI：10.1016/s0040-4039(03)01024-4

  日期：2003.6

  The stereoselective total synthesis of the proposed structures P1 and P2 for passifloricin A was achieved in 12 steps from n-hexadecanal by using enantioselective allyltitanations and a ring closing metathesis reaction as the key steps. Both PI and P2 are different from passifloricin A. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Antiparasite and antimycobacterial activity of passifloricin analogues
  作者：Wilson Cardona、Winston Quiñones、Sara Robledo、Ivan Darío Vélez、Juan Murga、Jorge García-Fortanet、Miguel Carda、Diana Cardona、Fernando Echeverri

  DOI：10.1016/j.tet.2006.02.017

  日期：2006.4

  Several structural analogues of the polyketide passifloricin lactone were synthesized using asymmetric stereoselective allylations and ring-closing methateses as key reactions. These compounds were active in vitro against intracellular amastigotes of Leishmania panamensis (strain UA 140), trophozoites of Plasinodium falciparum (strain NF54), and Mycobacterium tuberculosis (strain H(37)Rv). However, in spite of the significative antiparasitic activity of some synthetic analogues a high cytotoxicity was also observed. Based on these results a lactam derivative was also synthesized. This compound maintained a good level of activity with less toxicity. (c) 2006 Elsevier Ltd. All fights reserved.
• Stereoselective Synthesis of the Antiprotozoal Lactone Passifloricin A and Seven Isomers Thereof
  作者：Juan Murga、Jorge García-Fortanet、Miguel Carda、J. Alberto Marco

  DOI：10.1021/jo049275d

  日期：2004.10.1

  The conjugated δ-lactone passifloricin A, a natural product with antiprotozoal activity, and seven isomers thereof have been synthesized in enantiopure form. It has been shown in this way that the proposed structure for the natural compound was erroneous. The correct structure is now evidenced. Key steps of the syntheses were asymmetric Brown-type aldehyde allylations and ring-closing metatheses.

  具有对原生动物活性的天然产物共轭的δ-内酯西番莲菌素A及其七个异构体以对映体纯的形式合成。已经表明以这种方式提出的天然化合物的结构是错误的。现在证明了正确的结构。合成的关键步骤是不对称的布朗型醛烯丙基化和闭环复分解。
• Total Synthesis of Cryptocaryol A by Enantioselective Iridium-Catalyzed Alcohol C−H Allylation
  作者：Felix Perez、Andrew R. Waldeck、Michael J. Krische

  DOI：10.1002/anie.201600591

  日期：2016.4.11

  product cryptocaryol A is prepared in 8 steps via iridium catalyzed enantioselective diol double C−H allylation, which directly generates an acetate‐based triketide stereodiad. In 4 previously reported total syntheses, 17–28 steps were required.

  通过铱催化的对映选择性二醇双CHH烯丙基化反应可分8个步骤制备聚酮化合物天然产物隐香碳烯醇A，该化合物可直接生成基于乙酸盐的三酮化合物立体二胺。在先前报告的4个总合成中，需要17-28个步骤。