8-[(2-Methoxyphenyl)methyl]-9-(naphthalen-1-ylmethyl)-2-oxa-5,8,9-triaza-1-phosphabicyclo[3.3.3]undecane | 1293980-14-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-[(2-Methoxyphenyl)methyl]-9-(naphthalen-1-ylmethyl)-2-oxa-5,8,9-triaza-1-phosphabicyclo[3.3.3]undecane
• 英文别名: 8-[(2-methoxyphenyl)methyl]-9-(naphthalen-1-ylmethyl)-2-oxa-5,8,9-triaza-1-phosphabicyclo[3.3.3]undecane
• CAS: 1293980-14-9
• 化学式: C₂₅H₃₀N₃O₂P
• 分子量: 435.506
• InChiKey: XCHUNYOAUQKWAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  8-[(2-Methoxyphenyl)methyl]-9-(naphthalen-1-ylmethyl)-2-oxa-5,8,9-triaza-1-phosphabicyclo[3.3.3]undecane 在 双(三甲基硅基)过氧化物 作用下， 以 甲苯 为溶剂， 反应 14.0h， 以80%的产率得到8-[(2-Methoxyphenyl)methyl]-9-(naphthalen-1-ylmethyl)-1-oxido-2-oxa-5,8,9-triaza-1-phosphoniabicyclo[3.3.3]undecane
  参考文献：
  名称：

  First synthesis of P-chirogenic prophosphatranes

  摘要：

  Syntheses are reported for the novel P-chirogenic bicyclic prophosphatranes P(RNCH2CH2)(2)N(OCH2CH2)-(8) in which the two R groups [i.e., 1-methylenenaphthyl and 1,2-methoxybenzyl (8)] and in its corresponding phosphine oxide (9) are different. Also synthesized was the transannulated protonated phosphatrane cation in the salt [HP(RNCH2CH2)(3)N]Cl in which the three R groups [i.e., 1-methylenenaphthyl, 1,2-methoxybenzyl, and (S)-1-phenethyl (14)] are different, and also in its corresponding deprotonated prophosphatrane form P(RNCH2CH2)(3)N (15). Good analytical resolution of racemic 9 is reported, whereas only partial resolution was achieved for diastereomeric 14. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.041
• 作为产物：
  描述：

  2-[二(2-氨基乙基)氨基]乙醇 在 盐酸 、 sodium tetrahydroborate 、 potassium tert-butylate 、 水 、 三(二甲胺基)膦 、 三氯化磷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙腈 为溶剂， 反应 71.0h， 生成 8-[(2-Methoxyphenyl)methyl]-9-(naphthalen-1-ylmethyl)-2-oxa-5,8,9-triaza-1-phosphabicyclo[3.3.3]undecane
  参考文献：
  名称：

  First synthesis of P-chirogenic prophosphatranes

  摘要：

  Syntheses are reported for the novel P-chirogenic bicyclic prophosphatranes P(RNCH2CH2)(2)N(OCH2CH2)-(8) in which the two R groups [i.e., 1-methylenenaphthyl and 1,2-methoxybenzyl (8)] and in its corresponding phosphine oxide (9) are different. Also synthesized was the transannulated protonated phosphatrane cation in the salt [HP(RNCH2CH2)(3)N]Cl in which the three R groups [i.e., 1-methylenenaphthyl, 1,2-methoxybenzyl, and (S)-1-phenethyl (14)] are different, and also in its corresponding deprotonated prophosphatrane form P(RNCH2CH2)(3)N (15). Good analytical resolution of racemic 9 is reported, whereas only partial resolution was achieved for diastereomeric 14. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.041

文献信息

• First synthesis of P-chirogenic prophosphatranes
  作者：Yibo Zhou、Daniel W. Armstrong、Ying Zhang、John G. Verkade

  DOI：10.1016/j.tetlet.2011.01.041

  日期：2011.4

  Syntheses are reported for the novel P-chirogenic bicyclic prophosphatranes P(RNCH2CH2)(2)N(OCH2CH2)-(8) in which the two R groups [i.e., 1-methylenenaphthyl and 1,2-methoxybenzyl (8)] and in its corresponding phosphine oxide (9) are different. Also synthesized was the transannulated protonated phosphatrane cation in the salt [HP(RNCH2CH2)(3)N]Cl in which the three R groups [i.e., 1-methylenenaphthyl, 1,2-methoxybenzyl, and (S)-1-phenethyl (14)] are different, and also in its corresponding deprotonated prophosphatrane form P(RNCH2CH2)(3)N (15). Good analytical resolution of racemic 9 is reported, whereas only partial resolution was achieved for diastereomeric 14. (C) 2011 Elsevier Ltd. All rights reserved.