ethyl (E)-(4RS,5RS)-4,5-dihydroxy-5,9-dimethyl-2,8-decadienoate

• 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: ethyl (E)-(4RS,5RS)-4,5-dihydroxy-5,9-dimethyl-2,8-decadienoate
• 英文别名: ethyl (2E,4R,5R)-4,5-dihydroxy-5,9-dimethyldeca-2,8-dienoate
• 化学式: C₁₄H₂₄O₄
• 分子量: 256.342
• InChiKey: QCAMWQBPTMFNRV-UWCZFHCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (E)-(4RS,5RS)-4,5-dihydroxy-5,9-dimethyl-2,8-decadienoate 在 吡啶 、 甲基磺酰氯 、 potassium carbonate 作用下， 以 二氯甲烷 、 乙醇 为溶剂， 反应 3.5h， 生成 ethyl (E)-(4RS,5SR)-4,5-epoxy-5,9-dimethyl-2,8-decadienoate
  参考文献：
  名称：

  Stereospecific interconversion of cis- and trans-γ,δ-epoxy α,β-unsaturated ester systems

  摘要：

  The unprecedented, stereospecific interconversion of cis- and trans-gamma,delta-epoxy alpha,beta-unsaturated ester systems has been realized, which involves the palladium-catalyzed stereospecific alkoxy or hydroxy substitution reaction with double inversion of configuration at the gamma-position as the key step. The new methodology is not only applicable to various disubstituted and trisubstituted epoxy unsaturated esters, but also these interconversions proceed with an extremely high degree of stereoselectivity and efficiency. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.10.084
• 作为产物：
  描述：

  3,7-二甲基-2,6-辛二烯-1-醇 在 四(三苯基膦)钯 硼酸 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 0.17h， 生成 ethyl (E)-(4RS,5RS)-4,5-dihydroxy-5,9-dimethyl-2,8-decadienoate
  参考文献：
  名称：

  钯催化γ,δ-环氧-α,β-不饱和酯与硼酸的立体有择环氧化物开环反应生成具有双构型双反转的γ,δ-二醇衍生物

  摘要：

  已经开发了一种新的钯催化的 γ,δ-环氧-α,β-不饱和酯与硼酸的环氧化物开环反应，该反应进行立体定向，生成相应的 γ,δ-二...

  DOI：

  10.1246/cl.2004.764

文献信息

• Palladium-catalyzed stereospecific epoxide-opening reaction of γ,δ-epoxy-α,β-unsaturated esters with an alkylboronic acid leading to γ,δ-vicinal diols with double inversion of the configuration
  作者：Atsushi Hirai、Xiao-Qiang Yu、Terumichi Tonooka、Masaaki Miyashita

  DOI：10.1039/b307390d

  日期：——

  A palladium-catalyzed stereospecific epoxide-opening reaction of gamma,delta-epoxy-alpha,beta-unsaturated esters with an alkylboronic acid leading to gamma,delta-vicinal diols is described, which proceeds with retention of the configuration, i.e., via two consecutive S(N)2 processes, to afford the corresponding gamma,delta-cyclic boronates in high yields.

  描述了γ-δ-环氧-α-β-不饱和酯与烷基硼酸的钯催化的立体有择环氧化物开环反应，生成γ-δ-邻位二醇，该反应继续保持构型，即通过两个连续的S（N）2的过程，以高收率提供相应的γ，δ环硼酸盐。
• Stereospecific interconversion of cis- and trans-γ,δ-epoxy α,β-unsaturated ester systems
  作者：Xiao-Qiang Yu、Fumihiko Yoshimura、Keiji Tanino、Masaaki Miyashita

  DOI：10.1016/j.tetlet.2008.10.084

  日期：2008.12

  The unprecedented, stereospecific interconversion of cis- and trans-gamma,delta-epoxy alpha,beta-unsaturated ester systems has been realized, which involves the palladium-catalyzed stereospecific alkoxy or hydroxy substitution reaction with double inversion of configuration at the gamma-position as the key step. The new methodology is not only applicable to various disubstituted and trisubstituted epoxy unsaturated esters, but also these interconversions proceed with an extremely high degree of stereoselectivity and efficiency. (C) 2008 Elsevier Ltd. All rights reserved.
• Palladium-catalyzed Stereospecific Epoxide-opening Reaction of γ,δ-Epoxy-α,β-unsaturated Esters with Boric Acid Leading to γ,δ-Diol Derivatives with Double Inversion of Configuration
  作者：Xiao-Qiang Yu、Atsushi Hirai、Masaaki Miyashita

  DOI：10.1246/cl.2004.764

  日期：2004.6

  A new palladium-catalyzed epoxide-opening reaction of γ,δ-epoxy-α,β-unsaturated esters with boric acid has been developed, which proceeds stereospecifically giving rise to the corresponding γ,δ-dio...

  已经开发了一种新的钯催化的 γ,δ-环氧-α,β-不饱和酯与硼酸的环氧化物开环反应，该反应进行立体定向，生成相应的 γ,δ-二...