1-Dimethoxyphosphoryl-17-hydroxyheptadecan-2-one | 1004537-59-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: 1-Dimethoxyphosphoryl-17-hydroxyheptadecan-2-one
• CAS: 1004537-59-0
• 化学式: C₁₉H₃₉O₅P
• 分子量: 378.489
• InChiKey: PLVMGLOLVMLSMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-Dimethoxyphosphoryl-17-hydroxyheptadecan-2-one 、 苯乙醛 在 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  Synthesis of (+)-Didemniserinolipid B via Ketalization/Ring-Closing Metathesis

  摘要：

  A modular synthesis of didemniserinolipid B is reported. Central to this synthesis was the use of a ketalization/ring-closing metathesis (K/RCM) strategy to establish the 6,8-dioxabicyclo[3.2.1]octane core. The C10 axial alcohol was established via a selective epoxidation, followed by reductive trans-diaxial epoxide opening. The serinol and unsaturated ester side chains were introduced by a Williamson etherification and cross metathesis, respectively.

  DOI：

  10.1021/ol702454m
• 作为产物：
  描述：

  氧杂环十七烷-2-酮 、 甲基膦酸二甲酯 在 正丁基锂 、 氯化铵 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 2.59h， 生成 1-Dimethoxyphosphoryl-17-hydroxyheptadecan-2-one
  参考文献：
  名称：

  （+）-去氨二脂基脂质B的合成：2-烯丙基-4-氟苯基助剂在闭环复分解反应中的应用。

  摘要：

  描述了利用缩酮化/闭环复分解（K / RCM）策略合成双屈乳香脂素B。在这项工作的过程中，开发了一种新型的2-烯丙基-4-氟苯基助剂用于闭环复分解（RRCM），提高了RCM的收率。通过互补的二羟基化和环氧化途径将所得的6,8-二氧杂双环[3.2.1]辛烯核选择性官能化，以安装C10轴向醇。该双环缩酮核心通过醚化和带有不饱和α-苯基硒烯基酯的烯烃交叉复分解而进一步官能化，以完成总合成。

  DOI：

  10.1021/jo801666t

文献信息

• Formal total synthesis of (+)-didemniserinolipid B
  作者：Kavirayani R. Prasad、Vasudeva Rao Gandi

  DOI：10.1016/j.tetasy.2010.11.006

  日期：2010.12

  The formal total synthesis of (+)-didemniserinolipid B, a marine tunicate possessing a 6,8-dioxabicyclo[3.2.1]octane framework, was accomplished starting from L-(+)-tartaric acid. The key transformations in the synthesis include the elaboration of a gamma-hydroxy-amide readily obtained by desymmetrization of tartaric acid bis-amide via the controlled addition of a Grignard reagent followed by stereoselective reduction of the resulting ketone. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of (+)-Didemniserinolipid B: Application of a 2-Allyl-4-fluorophenyl Auxiliary for Relay Ring-Closing Metathesis
  作者：Christopher C. Marvin、Eric A. Voight、Judy M. Suh、Christopher L. Paradise、Steven D. Burke

  DOI：10.1021/jo801666t

  日期：2008.11.7

  work, a novel 2-allyl-4-fluorophenyl auxiliary for relay ring-closing metathesis (RRCM) was developed, which increased the yield of the RCM. The resulting 6,8-dioxabicyclo[3.2.1]octene core was selectively functionalized by complimentary dihydroxylation and epoxidation routes to install the C10 axial alcohol. This bicyclic ketal core was further functionalized by etherification and an alkene cross metathesis

  描述了利用缩酮化/闭环复分解（K / RCM）策略合成双屈乳香脂素B。在这项工作的过程中，开发了一种新型的2-烯丙基-4-氟苯基助剂用于闭环复分解（RRCM），提高了RCM的收率。通过互补的二羟基化和环氧化途径将所得的6,8-二氧杂双环[3.2.1]辛烯核选择性官能化，以安装C10轴向醇。该双环缩酮核心通过醚化和带有不饱和α-苯基硒烯基酯的烯烃交叉复分解而进一步官能化，以完成总合成。
• Synthesis of (+)-Didemniserinolipid B via Ketalization/Ring-Closing Metathesis
  作者：Christopher C. Marvin、Eric A. Voight、Steven D. Burke

  DOI：10.1021/ol702454m

  日期：2007.12.1

  A modular synthesis of didemniserinolipid B is reported. Central to this synthesis was the use of a ketalization/ring-closing metathesis (K/RCM) strategy to establish the 6,8-dioxabicyclo[3.2.1]octane core. The C10 axial alcohol was established via a selective epoxidation, followed by reductive trans-diaxial epoxide opening. The serinol and unsaturated ester side chains were introduced by a Williamson etherification and cross metathesis, respectively.