(R)-4-octylcyclopent-2-enone | 1268607-21-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-4-octylcyclopent-2-enone
• 英文别名: (R)-4-n-octycyclopent-2-enone；(+)-4-n-octycyclopent-2-enone；(4R)-4-octylcyclopent-2-en-1-one
• CAS: 1268607-21-1
• 化学式: C₁₃H₂₂O
• 分子量: 194.317
• InChiKey: JWIQVTZFBBTAKY-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-4-octylcyclopent-2-enone 在 aluminum oxide 、 正丁基锂 、 异丙胺 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.67h， 生成 (+)-TEI 9826
  参考文献：
  名称：

  Stereocontrolled synthesis of enantiopure anticancer cyclopentenone prostaglandin analogues: (−)- and (+)-TEI-9826

  摘要：

  The synthesis of both enantiomers of TEI-9826 has been accomplished in seven steps with an overall yield of 44% starting from diastereomeric camphor protected 3-[(dimethoxyphosphoryl)methyl]-4,5-dihydroxycyclopent-2-enones. The key steps include a fully diastereoselective hydrogenation of the endocyclic carbon-carbon double bond in the cyclopentenone ring controlled with a chiral diol moiety and the conversion of the latter into a new transposed olefinic bond. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.11.007
• 作为产物：
  描述：

  (1'R,2R,3aR,4'R,6aR)-6-(dimethoxyphosphorylmethyl)-1',7',7'-trimethylspiro[3a,6a-dihydrocyclopenta[d][1,3]dioxole-2,2'-bicyclo[2.2.1]heptane]-4-one 在 aluminum amalgam 、 10% palladium on activated carbon 、 氢气 、 lithium perchlorate 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 水 为溶剂， 反应 53.75h， 生成 (R)-4-octylcyclopent-2-enone
  参考文献：
  名称：

  Stereocontrolled synthesis of enantiopure anticancer cyclopentenone prostaglandin analogues: (−)- and (+)-TEI-9826

  摘要：

  The synthesis of both enantiomers of TEI-9826 has been accomplished in seven steps with an overall yield of 44% starting from diastereomeric camphor protected 3-[(dimethoxyphosphoryl)methyl]-4,5-dihydroxycyclopent-2-enones. The key steps include a fully diastereoselective hydrogenation of the endocyclic carbon-carbon double bond in the cyclopentenone ring controlled with a chiral diol moiety and the conversion of the latter into a new transposed olefinic bond. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.11.007

文献信息

• Iridium-Catalyzed Enantioselective Allylic Substitution of Unstabilized Enolates Derived from α,β-Unsaturated Ketones
  作者：Ming Chen、John F. Hartwig

  DOI：10.1002/anie.201403844

  日期：2014.8.11

  We report Ir‐catalyzed, enantioselective allylic substitution reactions of unstabilized silyl enolates derived from α,β‐unsaturated ketones. Asymmetric allylic substitution of a variety of allylic carbonates with silyl enolates gave allylated products in 62–94 % yield with 90–98 % ee and >20:1 branched‐to‐linear selectivity. The synthetic utility of this method was illustrated by the short synthesis

  我们报告了衍生自 α,β-不饱和酮的不稳定甲硅烷基烯醇化物的 Ir 催化的对映选择性烯丙基取代反应。用甲硅烷基烯醇化物对各种烯丙基碳酸酯进行不对称烯丙基取代得到烯丙基化产物，产率为 62-94%，ee为 90-98% ，支链至线性选择性 >20:1。抗癌剂 TEI-9826 的短合成说明了该方法的合成效用。
• Stereocontrolled synthesis of enantiopure anticancer cyclopentenone prostaglandin analogues: (−)- and (+)-TEI-9826
  作者：Remigiusz Żurawiński、Maciej Mikina、Marian Mikołajczyk

  DOI：10.1016/j.tetasy.2010.11.007

  日期：2010.12

  The synthesis of both enantiomers of TEI-9826 has been accomplished in seven steps with an overall yield of 44% starting from diastereomeric camphor protected 3-[(dimethoxyphosphoryl)methyl]-4,5-dihydroxycyclopent-2-enones. The key steps include a fully diastereoselective hydrogenation of the endocyclic carbon-carbon double bond in the cyclopentenone ring controlled with a chiral diol moiety and the conversion of the latter into a new transposed olefinic bond. (C) 2010 Elsevier Ltd. All rights reserved.