(R)-5-heptene-1,2-diol | 204120-73-0

• 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: (R)-5-heptene-1,2-diol
• 英文别名: (2R)-hept-6-ene-1,2-diol
• CAS: 204120-73-0
• 化学式: C₇H₁₄O₂
• 分子量: 130.187
• InChiKey: MMKZGAYMWPTUJT-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-5-heptene-1,2-diol 在 原乙酸三甲酯 、 乙酰溴 、 4-甲基苯磺酸吡啶 、 三乙基硼氢化锂 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 4.25h， 生成 2(S)-羟基庚-6-烯
  参考文献：
  名称：

  反式或顺式-2,6-二取代哌啶的一般不对称路线。（+）-9-epi-6-epipinidinol和（-）-pinidinol的第一个全合成

  摘要：

  从1,6-庚二烯开始，两个AD反应以逐步方式逐步生成抗-1,5-二醇和syn -1,5-二醇立体异构体，它们已通过氨基环化反应转化为反式-和顺式-2,6二取代的哌啶（反式-和顺- 12），分别。9表- 6- epipinidinol（ - （+）的第一个全合成2）和（ - ） - pinidinol（3）已经从实现反式和-顺式- 12。

  DOI：

  10.1016/s0040-4020(98)00831-x
• 作为产物：
  描述：

  1,6-庚二烯 在 AD-mix-α 作用下， 以 水 、 叔丁醇 为溶剂， 反应 24.0h， 生成 (-)-(S)-hept-6-ene-1,2-diol 、 (R)-5-heptene-1,2-diol
  参考文献：
  名称：

  Symmetry-Assisted Synthesis of C₂-Symmetric trans-α,α‘-Bis(hydroxymethyl)pyrrolidine and -piperidine Derivatives via Double Sharpless Asymmetric Dihydroxylation of α,ω-Terminal Dienes

  摘要：

  A new strategy has been developed for the synthesis of C-2-symmetric trans-alpha,alpha'-bis(hydroxymethyl)pyrrolidine and piperidine derivatives 1-3 starting from symmetric alpha,omega-terminal dienes 4-6. The double-asymmetric dihydroxylation (AD) reaction of 4-6 gave C-2-symmetric tetrols, which were converted in a four-step sequence to C-2-symmetric azacycloalkanes 17, 9, and 22, respectively. These azacycloalkanes were transformed into 1-3 in high enantiomeric excess (82% --> 98%ee). The double AD reaction proved to cause enantiomeric enhancement, even though the asymmetric induction for the first AD reaction is moderate. In addition, it was observed that the chromatography on silica gel of several C-2-symmetric azacycloalkanes (17, 20, and 22) of varying ee's resulted in marked enantiomeric fractionation.

  DOI：

  10.1021/jo971995f

文献信息

• Synthetic Studies on a Marine Natural Product, Palmerolide A: Synthesis of C1-C9 and C15-C21 Fragments
  作者：Krishna Kaliappan、Parthasarathy Gowrisankar

  DOI：10.1055/s-2007-982539

  日期：2007.6

  An efficient cross metathesis and Pd-catalyzed allylic rearrangement have been successfully used to construct the northern hemisphere of a cytotoxic marine natural product, palmerolide A.

  有效的交叉复分解和 Pd 催化的烯丙基重排已成功用于构建具有细胞毒性的海洋天然产物 Palmerolide A 的北半球。
• Shimizu, Masaki; Nemoto, Hideo; Kakuda, Hiroko, Heterocycles, 2003, vol. 59, # 1, p. 245 - 255
  作者：Shimizu, Masaki、Nemoto, Hideo、Kakuda, Hiroko、Takahata, Hiroki

  DOI：——

  日期：——
• Symmetry-Assisted Synthesis of <i>C</i>₂-Symmetric <i>trans</i>-α,α‘-Bis(hydroxymethyl)pyrrolidine and -piperidine Derivatives via Double Sharpless Asymmetric Dihydroxylation of α,ω-Terminal Dienes
  作者：Hiroki Takahata、Seiki Takahashi、Shin-ichi Kouno、Takefumi Momose

  DOI：10.1021/jo971995f

  日期：1998.4.1

  A new strategy has been developed for the synthesis of C-2-symmetric trans-alpha,alpha'-bis(hydroxymethyl)pyrrolidine and piperidine derivatives 1-3 starting from symmetric alpha,omega-terminal dienes 4-6. The double-asymmetric dihydroxylation (AD) reaction of 4-6 gave C-2-symmetric tetrols, which were converted in a four-step sequence to C-2-symmetric azacycloalkanes 17, 9, and 22, respectively. These azacycloalkanes were transformed into 1-3 in high enantiomeric excess (82% --> 98%ee). The double AD reaction proved to cause enantiomeric enhancement, even though the asymmetric induction for the first AD reaction is moderate. In addition, it was observed that the chromatography on silica gel of several C-2-symmetric azacycloalkanes (17, 20, and 22) of varying ee's resulted in marked enantiomeric fractionation.
• A general asymmetric route to trans- or cis-2,6-disubstituted piperidine. First total synthesis of (+)-9-epi-6-epipinidinol and (−)-pinidinol
  作者：Hiroki Takahata、Yasuhito Yotsui、Takefumi Momose

  DOI：10.1016/s0040-4020(98)00831-x

  日期：1998.10

  syn-1,5-diol stereodivergently, which have been converted by aminocyclization into trans- and cis-2,6-disubstituted piperidines (trans- and cis-12), respectively. The first total synthesis of (+)-9-epi-6-epipinidinol (2) and (−)-pinidinol (3) has been achieved from trans- and cis-12.

  从1,6-庚二烯开始，两个AD反应以逐步方式逐步生成抗-1,5-二醇和syn -1,5-二醇立体异构体，它们已通过氨基环化反应转化为反式-和顺式-2,6二取代的哌啶（反式-和顺- 12），分别。9表- 6- epipinidinol（ - （+）的第一个全合成2）和（ - ） - pinidinol（3）已经从实现反式和-顺式- 12。