ethyl (1-propyl-1-pentene)-H-phosphinate | 1070805-98-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: ethyl (1-propyl-1-pentene)-H-phosphinate
• CAS: 1070805-98-9
• 化学式: C₁₀H₂₁O₂P
• 分子量: 204.249
• InChiKey: NPTSHZOCFKCDIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  13.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 ethyl (1-propyl-1-pentene)-H-phosphinate 在 三乙胺 作用下， 反应 24.0h， 以853 mg的产率得到ethyl (hydroxymethyl)(1-propyl-1-pentene)phosphinate
  参考文献：
  名称：

  Chemistry of the Versatile (Hydroxymethyl)phosphinyl P(O)CH₂OH Functional Group

  摘要：

  (Hydroxymethyl)phosphorus compounds are well-known and valuable compounds in general; however the use of (hydroxymethyl)phosphinates (RP)-P-1(O)(OR2)CH2OH in particular has been much more limited. The potential of this functionality has not yet been fully realized because the mild unmasking of the hydroxymethyl group was not available. The mild oxidative conversion of (RP)-P-1(O)(OR2)CH2OH into (RP)-P-1(O)(OR2)H using the Corey-Kim oxidation is described. Other reactions preserving the methylene carbon are also reported.

  DOI：

  10.1021/ol3013793
• 作为产物：
  描述：

  ethyl (hydroxymethyl)(1-propyl-1-pentene)phosphinate 在 N-氯代丁二酰亚胺 、 二甲基硫 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.58h， 以75%的产率得到ethyl (1-propyl-1-pentene)-H-phosphinate
  参考文献：
  名称：

  Chemistry of the Versatile (Hydroxymethyl)phosphinyl P(O)CH₂OH Functional Group

  摘要：

  (Hydroxymethyl)phosphorus compounds are well-known and valuable compounds in general; however the use of (hydroxymethyl)phosphinates (RP)-P-1(O)(OR2)CH2OH in particular has been much more limited. The potential of this functionality has not yet been fully realized because the mild unmasking of the hydroxymethyl group was not available. The mild oxidative conversion of (RP)-P-1(O)(OR2)CH2OH into (RP)-P-1(O)(OR2)H using the Corey-Kim oxidation is described. Other reactions preserving the methylene carbon are also reported.

  DOI：

  10.1021/ol3013793

文献信息

• Phosphorus-Carbon Bond Formation: Palladium-Catalyzed Cross-Coupling of<i>H</i>-Phosphinates and Other P(O)H-Containing Compounds
  作者：Olivier Berger、Christelle Petit、Eric L. Deal、Jean-Luc Montchamp

  DOI：10.1002/adsc.201300069

  日期：2013.5.3

  developed for the cross‐coupling of P(O)H compounds with Csp2X and related partners. Palladium catalysis using a ligand/additive combination, typically either xantphos/ethylene glycol or 1,1′‐bis(diphenylphosphino)ferrocene/1,2‐dimethoxyethane, with diisopropylethylamine as the base, proved to be generally useful for the synthesis of numerous PC containing compounds. Routinely, 2 mol% of catalyst are

  两个普遍适用的系统已被开发为P的交叉偶联（O）H的化合物为C SP2  X和相关的合作伙伴。使用配体/添加剂组合（通常为黄磷/乙二醇或1,1'-双（二苯基膦基）二茂铁/ 1,2-二甲氧基乙烷，以二异丙基乙胺为碱）催化钯，通常可用于合成许多P 含C的化合物。通常使用2摩尔％的催化剂（少于大多数其他文献报道中通常使用的量的一半）。在大多数情况下，使用各种亲电试剂（RX，其中R =烯基，烯丙基，炔基等）可获得出色的结果。公开了我们研究的全部内容，包括双氢磷酰化/偶联和双催化磷碳键形成的偶联/偶联。该方法可与任何现有文献报告相媲美。使用添加剂似乎是控制次膦基化合物的反应性的普遍有用的策略。