(R)_p-menthylmethylphenylphosphine | 65440-73-5

• 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: (R)_p-menthylmethylphenylphosphine
• 英文别名: (R_P)-Menthylmethylphenylphosphine；(S)_p-menthylmethylphenylphosphine；(S_P)-Menthylmethylphenylphosphine；P(Ph)(Me)((-)menthyl)；P(Ph)(Me)(Men)；R(P)-l-Menthylmethylphenylphosphin；methyl-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]-phenylphosphane
• CAS: 65440-73-5；65440-74-6
• 化学式: C₁₇H₂₇P
• 分子量: 262.375
• InChiKey: MROIONXWJFDDSP-JSWLAIEMSA-N

物化性质

• 沸点：
  95 °C(Press: 0.025 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (R)_p-menthylmethylphenylphosphine 在 双氧水 作用下， 以 苯 为溶剂， 反应 18.0h， 生成 (R_P)-Menthylmethylphenylphosphine Oxide
  参考文献：
  名称：

  Synthesis of phosphines having chiral organic groups ligated to chiral phosphorus

  摘要：

  DOI：

  10.1021/jo01306a030
• 作为产物：
  描述：

  L-menthylphenylchlorophosphine 在 盐酸 作用下， 以 乙醚 为溶剂， 反应 8.5h， 生成 (R)_p-menthylmethylphenylphosphine
  参考文献：
  名称：

  P -Stereogenic氯膦的亲核取代：机理，立体化学和非对映异构的二级膦氧化物向叔膦的立体选择性转化。

  摘要：

  通过用草酰氯处理，将次生氧化膦的非对映异构体立体定向转化为氯膦盐，该立体选择性生成P转化或保留的叔膦，具体取决于分别被脂肪族或芳香族格氏试剂取代，产率高达99％， 99：1博士 有人建议将π电子在芳基上排斥为磷上的孤电子对，以实现P保留取代。

  DOI：

  10.1021/acs.orglett.7b02667

文献信息

• Chirality Breeding via Asymmetric Phosphination. Palladium-Catalyzed Diastereoselective Synthesis of a P-Stereogenic Phosphine
  作者：Natalia F. Blank、Katherine C. McBroom、David S. Glueck、W. Scott Kassel、Arnold L. Rheingold

  DOI：10.1021/om050993f

  日期：2006.3.1

  Methylation of the crystallographically characterized primary alkylphosphine-borane PH(2)Men(BH3) (3, Men = (-)-menthyl) under phase-transfer conditions, followed by deprotection, gave the secondary phosphine PH(Me)(Men) (2). Cross-coupling of 2 with PhI in the presence of NaOSiMe3 selectively gave S-P-PPh(Me)(Men) (1, L) with a variety of Pd catalyst precursors, including a complex of diastereopure S-P-1, trans-PdL2(Ph)(I) (6a). In this reaction, the chiral phosphine L formally acted as a ligand in catalysis of its selective self-reproduction, but 6a was partially transformed to its diastereomers, trans-Pd(S-P-1)-(R-P-1)(Ph)(I) (6b) and trans-Pd(R-P-1)(2)(Ph)(1) (6c), and several other intermediates were observed during catalysis.
• Nucleophilic Substitution of <i>P</i>-Stereogenic Chlorophosphines: Mechanism, Stereochemistry, and Stereoselective Conversions of Diastereomeric Secondary Phosphine Oxides to Tertiary Phosphines
  作者：Jing-Jing Ye、Shao-Zhen Nie、Ji-Ping Wang、Jing-Hong Wen、Yu Zhang、Mao-Ran Qiu、Chang-Qiu Zhao

  DOI：10.1021/acs.orglett.7b02667

  日期：2017.10.6

  A diastereomeric mixture of secondary phosphine oxide is stereospecifically converted to chlorophosphine salt by treatment with oxalyl chloride, which stereoselectively affords P-inverted or retained tertiary phosphines, depending on the substitution with aliphatic or aromatic Grignard reagents, respectively, in high to 99% yield and 99:1 dr. The repulsion of π-electron on aryl to lone electron pair

  通过用草酰氯处理，将次生氧化膦的非对映异构体立体定向转化为氯膦盐，该立体选择性生成P转化或保留的叔膦，具体取决于分别被脂肪族或芳香族格氏试剂取代，产率高达99％， 99：1博士 有人建议将π电子在芳基上排斥为磷上的孤电子对，以实现P保留取代。
• Synthesis of phosphines having chiral organic groups ligated to chiral phosphorus
  作者：Donald Valentine、John F. Blount、Katherine Toth

  DOI：10.1021/jo01306a030

  日期：1980.8