trans-2,2-dimethyl-3-<3-methyl-7-oxo-3(E)-octenyl>cyclopropanecarbaldehyde | 100693-05-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-2,2-dimethyl-3-<3-methyl-7-oxo-3(E)-octenyl>cyclopropanecarbaldehyde
• 英文别名: trans-2,2-Dimethyl-3-(3-methyl-7-oxo-3E-octenyl)cyclopropanecarbaldehyde；(+/-)-Anthoplanone；(1R,3R)-2,2-dimethyl-3-[(E)-3-methyl-7-oxooct-3-enyl]cyclopropane-1-carbaldehyde
• CAS: 100693-05-8；100762-47-8
• 化学式: C₁₅H₂₄O₂
• 分子量: 236.354
• InChiKey: OWXSNWCHPCHSFO-GFUGXAQUSA-N

物化性质

• 沸点：
  327.7±15.0 °C(Predicted)
• 密度：
  0.977±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-2,2-dimethyl-3-<3-methyl-7-oxo-3(E)-octenyl>cyclopropanecarbaldehyde 、 三氯化钛 以31%的产率得到
  参考文献：
  名称：

  MCMURRY, JOHN E.;BOSCH, GREGORY K., J. ORG. CHEM., 52,(1987) N 22, 4885-4893

  摘要：

  DOI：
• 作为产物：
  描述：

  香叶基丙酮 在 氢氧化钾 、 lithium aluminium tetrahydride 、 sodium acetate 、 铜 、 potassium carbonate 、 pyridinium chlorochromate 、 锌 、 三氯氧磷 作用下， 以 乙醚 、 二氯甲烷 、 水 、 溶剂黄146 、 丙酮 为溶剂， 生成 trans-2,2-dimethyl-3-<3-methyl-7-oxo-3(E)-octenyl>cyclopropanecarbaldehyde
  参考文献：
  名称：

  Synthesis of bicyclogermacrene and lepidozene

  摘要：

  DOI：

  10.1016/s0040-4039(00)98952-4

文献信息

• Total Synthesis and Absolute Configuration of (−)-Anthoplalone
  作者：Stephen Hanessian、Louis-David Cantin、Daniele Andreotti

  DOI：10.1021/jo990302n

  日期：1999.6.1

  We report the total synthesis of the cytotoxic agent (-)-anthoplalone and the determination of its absolute stereochemistry. The cyclopropane moiety was prepared using a nonracemic bicyclic chloroallyl phosphonamide anion addition to tert-butyl 3,3-dimethyl acrylate. Several pathways were studied to secure the E-trisubstituted olefin of the left part of the molecule.

  我们报告了细胞毒剂（-）-anthoplalone的总合成及其绝对立体化学的测定。使用非外消旋的双环氯烯丙基膦酰胺阴离子加到丙烯酸3，3-二甲基叔丁酯中制备环丙烷部分。研究了几种途径来确保分子左部分的E-三取代烯烃。
• In vivo and in vitro olefin cyclopropanation catalyzed by heme enzymes
  申请人：California Institute of Technology

  公开号：US10208322B2

  公开（公告）日：2019-02-19

  The present invention provides methods for catalyzing the conversion of an olefin to any compound containing one or more cyclopropane functional groups using heme enzymes. In certain aspects, the present invention provides a method for producing a cyclopropanation product comprising providing an olefinic substrate, a diazo reagent, and a heme enzyme; and admixing the components in a reaction for a time sufficient to produce a cyclopropanation product. In other aspects, the present invention provides heme enzymes including variants and fragments thereof that are capable of carrying out in vivo and in vitro olefin cyclopropanation reactions. Expression vectors and host cells expressing the heme enzymes are also provided by the present invention.

  本发明提供了使用血红素酶催化烯烃向任何含有一个或多个环丙烷官能团的化合物转化的方法。在某些方面，本发明提供了一种生产环丙烷化产物的方法，包括提供烯烃底物、重氮试剂和血红素酶；以及在反应中将各组分混合足够长的时间以生产环丙烷化产物。在其他方面，本发明提供了能够进行体内和体外烯烃环丙烷化反应的血红素酶，包括其变体和片段。本发明还提供了表达血红素酶的表达载体和宿主细胞。
• Cytochrome P450 BM3 enzyme variants for preparation of cyclopropanes
  申请人：California Institute of Technology

  公开号：US11008596B2

  公开（公告）日：2021-05-18

  The present invention provides methods for catalyzing the conversion of an olefin to any compound containing one or more cyclopropane functional groups using heme enzymes. In certain aspects, the present invention provides a method for producing a cyclopropanation product comprising providing an olefinic substrate, a diazo reagent, and a heme enzyme; and admixing the components in a reaction for a time sufficient to produce a cyclopropanation product. In other aspects, the present invention provides heme enzymes including variants and fragments thereof that are capable of carrying out in vivo and in vitro olefin cyclopropanation reactions. Expression vectors and host cells expressing the heme enzymes are also provided by the present invention.

  本发明提供了利用血红素酶催化烯烃向任何含有一个或多个环丙烷官能团的化合物转化的方法。在某些方面，本发明提供了一种生产环丙烷化产物的方法，包括提供烯烃底物、重氮试剂和血红素酶；以及在反应中将各组分混合足够长的时间以生产环丙烷化产物。在其他方面，本发明提供了能够进行体内和体外烯烃环丙烷化反应的血红素酶，包括其变体和片段。本发明还提供了表达血红素酶的表达载体和宿主细胞。
• Synthesis of macrocyclic terpenoid hydrocarbons by intramolecular carbonyl coupling: bicyclogermacrene, lepidozene, and casbene
  作者：John E. McMurry、Gregory K. Bosch

  DOI：10.1021/jo00231a012

  日期：1987.10
• Ring Contraction of Cyclobutanes and a Novel Cascade Reaction: Application to Synthesis of (.+-.)-Anthoplalone and (.+-.)-Lepidozene
  作者：Masataka Ihara、Takahiko Taniguchi、Yuji Tokunaga、Keiichiro Fukumoto

  DOI：10.1021/jo00105a028

  日期：1994.12

  Two efficient and practical synthetic methodologies for the construction of small ring systems have been developed. The first method involves a novel rearrangement of cyclobutanes 10 and 14 leading to cyclopropanes 11 and 15 employing BF3.OEt(2) or POCl3 in the presence of pyridine or Raney nickel. The second method utilizes a novel cascade reaction of alpha,beta-unsaturated esters 25 and 36 possessing a cyclopropyl ketone moiety with TMSI in the presence of(TMS)(2)NH to afford polycyclic cyclobutane derivatives 26 and 38. A synthesis of(+/-)-anthoplalone (41) and a formal synthesis of (+/-)-lepidozene (42) were achieved utilizing 15, obtained by the above method.