(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl 4-nitrobenzoate

• 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: (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl 4-nitrobenzoate
• 英文别名: trans,trans-farnesyl p-nitrobenzoate；[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl] 4-nitrobenzoate
• 化学式: C₂₂H₂₉NO₄
• 分子量: 371.477
• InChiKey: QVSQVPHLXXGQHZ-RKACFXBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl 4-nitrobenzoate 在 Oxone 、 Shi's ketone 、 四丁基硫酸氢铵 、 edetate disodium 、 potassium carbonate 作用下， 以 1,2-dimethoxymethane 、 水 、 乙腈 为溶剂， 以61%的产率得到[(E)-5-[(2R,3R)-3-[2-[(2R)-3,3-dimethyloxiran-2-yl]ethyl]-3-methyloxiran-2-yl]-3-methylpent-2-enyl] 4-nitrobenzoate
  参考文献：
  名称：

  Biomimetic Syntheses from Squalene-Like Precursors: Synthesis of ent-Abudinol B and Reassessment of the Structure of Muzitone

  摘要：

  We achieved the stereoselective syntheses of two different structural patterns corresponding to the enantiomers of the marine natural products abudinol B and muzitone, by developing two-directional tandem biomimetic cyclizations of polyepoxides of squalene analogues in which one alkene was functionalized as an enolsilane. In the course of this work, we demonstrated that the structure of muzitone was misassigned.

  DOI：

  10.1021/ja1006806
• 作为产物：
  描述：

  对硝基苯甲醇 、 反式,反式-金合欢醇 在 sodium carbonate 、 钯 、 silver(l) oxide 作用下， 反应 48.0h， 以64%的产率得到(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl 4-nitrobenzoate
  参考文献：
  名称：

  Pd-胶体催化/ Ag2O氧化的苄醇的一般和选择性酯化

  摘要：

  从Hermann-Beller palladacycle的降解中获得的钯胶体被证明是一种有效的催化体系，与氧化银作为选择性氧化剂结合使用，可在甲醇为溶剂的情况下对不同取代的苄醇进行氧化酯化。催化体系表现出的优异的反应性也使醇类偶合体从MeOH转变为具有各种功能的多种醇类。所开发方案的温和性还使得可以使用炔丙醇作为偶联伴侣，而没有观察到末端炔烃的任何干扰。使用开发的催化剂体系，在乙二醇和甘油的情况下，伯醇官能团相对于仲醇的选择性氧化偶联也是可能的。

  DOI：

  10.1002/asia.201900566

文献信息

• Catalytic diastereo- and positionselective oxidative mono-cyclization of 1,5,9-trienes and polyenes
  作者：Sabrina Göhler、Christian B. W. Stark

  DOI：10.1039/b702877f

  日期：——

  Ruthenium tetroxide (1 mol%) has been used as a catalyst for the oxidative mono-cyclization of 1,5,9-trienes and polyenes. The poly-unsaturated substrates underwent mono-cyclization with a high degree of diastereo- and positionselectivity to produce mono-tetrahydrofuran diols with a varying degree of unsaturation. Up to four new stereogenic centers were created in this single step transformation. The remarkable positionselectivity appears to be a result of relative electronic properties of the double bonds within the polyolefinic substrates in conjunction with conformational constraints.

  过氧化钌（1毫摩尔%）被用作1,5,9-三烯和多烯的氧化单环化反应的催化剂。多不饱和底物经历了具有高程度的Diastereo选择性和位点选择性的单环化反应，生成了不同程度不饱和的单烯四氢呋喃二醇。在这一单步转化中，最多可以创造四个新的立体中心。显著的位点选择性似乎是由于聚烯烃底物中双键的相对电子特性与构象约束的结合所导致的。
• Stereo- and Regioselective Synthesis of Squalene Tetraepoxide
  作者：Rongbiao Tong、Matthew A. Boone、Frank E. McDonald

  DOI：10.1021/jo901920d

  日期：2009.11.6

  Squalene tetraepoxide, it putative biosyntheic precursor to a variety of oxacyclic triterpenoid natural products, has been efficiently synthesized by anionic coupling of two farnesol-derived diepoxides, which have arisen from electronic control of the regioselectivity in organocatalytic enantioselective epoxidations.
• Pd‐Colloids‐Catalyzed/Ag ₂ O‐Oxidized General and Selective Esterification of Benzylic Alcohols
  作者：Vaibhav Sable、Jagrut Shah、Anuja Sharma、Anant R. Kapdi

  DOI：10.1002/asia.201900566

  日期：2019.8

  Palladium colloids obtained from the degradation of Hermann–Beller palladacycle proved to be an efficient catalytic system in combination with silver oxide as a selective oxidant for the oxidative esterification of differently substituted benzyl alcohols in MeOH as solvent. Excellent reactivity exhibited by the catalytic system also allowed the alcoholic coupling partner to be changed from MeOH to

  从Hermann-Beller palladacycle的降解中获得的钯胶体被证明是一种有效的催化体系，与氧化银作为选择性氧化剂结合使用，可在甲醇为溶剂的情况下对不同取代的苄醇进行氧化酯化。催化体系表现出的优异的反应性也使醇类偶合体从MeOH转变为具有各种功能的多种醇类。所开发方案的温和性还使得可以使用炔丙醇作为偶联伴侣，而没有观察到末端炔烃的任何干扰。使用开发的催化剂体系，在乙二醇和甘油的情况下，伯醇官能团相对于仲醇的选择性氧化偶联也是可能的。
• Biomimetic Syntheses from Squalene-Like Precursors: Synthesis of <i>ent-</i>Abudinol B and Reassessment of the Structure of Muzitone
  作者：Matthew A. Boone、Rongbiao Tong、Frank E. McDonald、Sheri Lense、Rui Cao、Kenneth I. Hardcastle

  DOI：10.1021/ja1006806

  日期：2010.4.14

  We achieved the stereoselective syntheses of two different structural patterns corresponding to the enantiomers of the marine natural products abudinol B and muzitone, by developing two-directional tandem biomimetic cyclizations of polyepoxides of squalene analogues in which one alkene was functionalized as an enolsilane. In the course of this work, we demonstrated that the structure of muzitone was misassigned.