3-epi-litsenolide D₂ | 386277-86-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3-epi-litsenolide D₂
• 英文别名: 3-epilitsenolide D₂；(3E,4R,5R)-3-dodecylidene-4-hydroxy-5-methyl-tetrahydrofuran-2-one；(3E,4R,5R)-3-dodecylidene-4-hydroxy-5-methyloxolan-2-one
• CAS: 386277-86-7
• 化学式: C₁₇H₃₀O₃
• 分子量: 282.423
• InChiKey: NSMMPEJLOMMKCX-AHZXUYQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-epi-litsenolide D₂ 在 10percent Pd/C 吡啶 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 Acetic acid (2R,3R,4S)-4-dodecyl-2-methyl-5-oxo-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Chemical Constituents from Alseodaphne andersonii

  摘要：

  Five new compounds, including four C-17 gamma-lactones, dihydroisoobtusilactone (A), dihydroobtusilactorie (2), 3-epilitsenolide D-2 (3), and 3-epilitsenolide D-1 (4), and one furanone alseodafuranone (V were isolated from the root and stem of Alseodaphne andersonii. Their structures were elucidated mainly by spectral analysis (NMR and MS) and partially by chemical correlation.

  DOI：

  10.1021/np010349f
• 作为产物：
  描述：

  methyl (E)-pent-3-enoate 在 AD-mix-α 、 甲基磺酰胺 、 三苯基膦 、 lithium diisopropyl amide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 150.0h， 生成 3-epi-litsenolide D₂
  参考文献：
  名称：

  Stereopure 1,3-butadiene-2-carboxylates and their conversion into non-racemic α-alkylidenebutyrolactone natural products by asymmetric dihydroxylation

  摘要：

  Dienoic esters 1 with the four possible permutations of the C=C configurations were prepared in two steps via non-stereoselective aldol additions followed by stereospecific beta -eliminations. Sharpless dihydroxylations of these esters yielded natural and unnatural alpha -alkylidene-beta -hydroxybutyrolactones 2. Among these were synthetic dihydromahubanolide B (cis,Z-2a), isodihydromahubanolide B (cis,E-2a) and, for the first time, litsenolide D-1 (ent-trans,Z-2b) and the enantiomer trans,E-2b of litsenolide D-2. Competitively, dihydroxyesters 10 were formed. (C) 2001 Elsevier Science Ltd. Al rights reserved.

  DOI：

  10.1016/s0040-4039(01)00598-6

文献信息

• Total Syntheses of 3-<i>epi</i>-Litsenolide D₂ and Lincomolide A
  作者：Noriki Kutsumura、Akito Kiriseko、Kentaro Niwa、Takao Saito

  DOI：10.1021/acs.joc.8b01825

  日期：2018.9.21

  The first total syntheses of 3-epi-litsenolide D2 and its enantiomer lincomolide A were achieved. The synthetic highlights of our approach include olefin cross metathesis and bromine addition to the generated double bond, followed by the regioselective HBr-elimination and intramolecular carbonylation using bis(triphenylphosphine)dicarbonylnickel. This investigation also revealed that the previously

  首次合成了3- epi- litsenolide D 2及其对映异构体lincomolideA。我们方法的合成亮点包括烯烃交叉复分解和向生成的双键中添加溴，然后使用双（三苯基膦）二羰基镍进行区域选择性HBr消除和分子内羰基化。这项研究还表明，应该修改以前报告的3- epi- litsenolide D 2的特定旋光度。