(-)-dimenthyl ethylphosphonate | 930596-97-7

• 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: (-)-dimenthyl ethylphosphonate
• 英文别名: (1S,2R,4R)-2-[ethyl-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxy-oxidophosphaniumyl]oxy-4-methyl-1-propan-2-ylcyclohexane
• CAS: 930596-97-7
• 化学式: C₂₂H₄₃O₃P
• 分子量: 386.555
• InChiKey: ANLYXTHENVOQMR-KQFPAPQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  41.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-dimenthyl ethylphosphonate 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 20.33h， 生成 (-)-dimenthyl 1-iodo-1-methyl-6-trimethylsilyl-n-hex-5-ynylphosphonate
  参考文献：
  名称：

  The difference in reactivity of (−)-mono and dimenthyl vs. diethyl alkylphosphonates in the α-lithiation reaction: Carbanionic synthesis of unknown (−)-dimenthyl 1-iodoalkylphosphonates and their first use in the radical iodine atom transfer addition (I-ATRA) and cyclisation (I-ATRC) reactions

  摘要：

  Unknown (-)-dimenthyl and ethyl (-)-menthyl 1-iodoethylphosphonates were synthesized via I-lithio derivatives in 85-87% yields. Starting (-)-dimenthyl alkylphosphonates (R = Me, Et, i-Pr) were obtained in the Michaelis-Becker reaction (75-81% yields) and/or in the methylation reaction of the corresponding 1-lithio-alkylphosphonates (78-92% yields). An interesting concentration and time correlations, never observed for diethyl alkylphosphonates, were found for the metalation of bulky (-)-menthyl alkylphosphonates with /IBuLi and general reaction conditions for the carbanion generation were elaborated. The first example of the I-ATRA reaction of (-)-dimenthyl 1-iodoethylphosphonate with 1-hexene (AIBN) gave four diastereomers (1.6:1:1:0.4), separated into two pairs. The 1-ATRC reaction was not effective due to a steric hindrance around the reactive center. The X-ray analysis of (-)-dimenthyl methylphosphonate confirmed a considerable steric hindrance in higher (-)-dimenthyl alkylphosphonate esters in comparison to their diethyl analogs. (c) 2006 Published by Elsevier B.V.

  DOI：

  10.1016/j.jorganchem.2006.10.069
• 作为产物：
  描述：

  L-薄荷醇 在 水 、 sodium hydride 、 三乙胺 、 三氯化磷 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 27.0h， 生成 (-)-dimenthyl ethylphosphonate
  参考文献：
  名称：

  The difference in reactivity of (−)-mono and dimenthyl vs. diethyl alkylphosphonates in the α-lithiation reaction: Carbanionic synthesis of unknown (−)-dimenthyl 1-iodoalkylphosphonates and their first use in the radical iodine atom transfer addition (I-ATRA) and cyclisation (I-ATRC) reactions

  摘要：

  Unknown (-)-dimenthyl and ethyl (-)-menthyl 1-iodoethylphosphonates were synthesized via I-lithio derivatives in 85-87% yields. Starting (-)-dimenthyl alkylphosphonates (R = Me, Et, i-Pr) were obtained in the Michaelis-Becker reaction (75-81% yields) and/or in the methylation reaction of the corresponding 1-lithio-alkylphosphonates (78-92% yields). An interesting concentration and time correlations, never observed for diethyl alkylphosphonates, were found for the metalation of bulky (-)-menthyl alkylphosphonates with /IBuLi and general reaction conditions for the carbanion generation were elaborated. The first example of the I-ATRA reaction of (-)-dimenthyl 1-iodoethylphosphonate with 1-hexene (AIBN) gave four diastereomers (1.6:1:1:0.4), separated into two pairs. The 1-ATRC reaction was not effective due to a steric hindrance around the reactive center. The X-ray analysis of (-)-dimenthyl methylphosphonate confirmed a considerable steric hindrance in higher (-)-dimenthyl alkylphosphonate esters in comparison to their diethyl analogs. (c) 2006 Published by Elsevier B.V.

  DOI：

  10.1016/j.jorganchem.2006.10.069