methyl (7R)-7,11-dimethyl-3-oxododec-10-enoate | 1019672-03-7

• 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: methyl (7R)-7,11-dimethyl-3-oxododec-10-enoate
• CAS: 1019672-03-7
• 化学式: C₁₅H₂₆O₃
• 分子量: 254.37
• InChiKey: PKBMGNSKHVTISU-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (7R)-7,11-dimethyl-3-oxododec-10-enoate 在 N-甲基咪唑 、 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium chlorite 、 sodium dihydrogenphosphate dihydrate 、 2-甲基-2-丁烯 、 L-(+)-酒石酸二异丙酯 、 三氧化硫吡啶 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 33.42h， 生成 methyl (2R,3S)-3-((R)-4,8-dimethylnon-7-en-1-yl)-3-methyloxirane-2-carboxylate
  参考文献：
  名称：

  Structure–activity relationship of novel juvenile hormone, JHSB3, isolated from the stink bug, Plautia stali

  摘要：

  The structure-activity relationship of JHSB(3) isolated from the pentatomid bug. Plautia stali, was studied. Various synthetic analogs were synthesized and subjected to the juvenilizing activity tests using the last instar nymphs of P. stali. These studies indicated that the coexistence of the ester carbonyl group, two epoxides at C2,3 and C10,11 were proved to be crucial for the potent juvenilizing activity. Among the tested analogs, we found highly potent analogs in which the C6,7 double bond of JHSB3 was saturated (0.1 mu g/insect). The methoxy analogs in which the epoxide moiety at C10,11 was substituted with a methoxy group exerted a moderate juvenilizing activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.080
• 作为产物：
  描述：

  (S)-3,7-dimethyloct-6-en-1-yl benzenesulfonate 、 乙酰乙酸甲酯 在 sodium hydride 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以65%的产率得到methyl (7R)-7,11-dimethyl-3-oxododec-10-enoate
  参考文献：
  名称：

  A Concise Synthesis of ent-Cholesterol

  摘要：

  ent-Cholesterol was synthesized in 16 steps,from commercially available (S)-citronellol. The overall yield for the synthesis was 2.0%. This route is amenable to gram-scale preparation of ent-cholesterol. Isotopic incorporation near the end of the synthesis was achieved using labeled methyl iodide. This synthesis is the most practical to date and will make ent-cholesterol more readily available to use as a probe of the function and metabolism of cholesterol.

  DOI：

  10.1021/jo702694g

文献信息

• A Concise Synthesis of <i>ent</i>-Cholesterol
  作者：Jitendra D. Belani、Scott D. Rychnovsky

  DOI：10.1021/jo702694g

  日期：2008.4.1

  ent-Cholesterol was synthesized in 16 steps,from commercially available (S)-citronellol. The overall yield for the synthesis was 2.0%. This route is amenable to gram-scale preparation of ent-cholesterol. Isotopic incorporation near the end of the synthesis was achieved using labeled methyl iodide. This synthesis is the most practical to date and will make ent-cholesterol more readily available to use as a probe of the function and metabolism of cholesterol.
• Structure–activity relationship of novel juvenile hormone, JHSB3, isolated from the stink bug, Plautia stali
  作者：Kanako Kaihara、Toyomi Kotaki、Hideharu Numata、Yasufumi Ohfune、Tetsuro Shinada

  DOI：10.1016/j.tet.2011.10.080

  日期：2012.1

  The structure-activity relationship of JHSB(3) isolated from the pentatomid bug. Plautia stali, was studied. Various synthetic analogs were synthesized and subjected to the juvenilizing activity tests using the last instar nymphs of P. stali. These studies indicated that the coexistence of the ester carbonyl group, two epoxides at C2,3 and C10,11 were proved to be crucial for the potent juvenilizing activity. Among the tested analogs, we found highly potent analogs in which the C6,7 double bond of JHSB3 was saturated (0.1 mu g/insect). The methoxy analogs in which the epoxide moiety at C10,11 was substituted with a methoxy group exerted a moderate juvenilizing activity. (C) 2011 Elsevier Ltd. All rights reserved.