2,2,6,6-Tetrakis-diisopropylamino-1,7-diaza-2λ⁵,6λ⁵-diphospha-indene-3,3a,4,5-tetracarboxylic acid tetramethyl ester | 158589-49-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,2,6,6-Tetrakis-diisopropylamino-1,7-diaza-2λ⁵,6λ⁵-diphospha-indene-3,3a,4,5-tetracarboxylic acid tetramethyl ester
• 英文别名: Tetramethyl 3,3,8,8-tetrakis[di(propan-2-yl)amino]-2,9-diaza-3lambda5,8lambda5-diphosphabicyclo[4.3.0]nona-1(9),2,4,7-tetraene-4,5,6,7-tetracarboxylate；tetramethyl 3,3,8,8-tetrakis[di(propan-2-yl)amino]-2,9-diaza-3λ5,8λ5-diphosphabicyclo[4.3.0]nona-1(9),2,4,7-tetraene-4,5,6,7-tetracarboxylate
• CAS: 158589-49-2
• 化学式: C₃₇H₆₈N₆O₈P₂
• 分子量: 786.93
• InChiKey: DYNKYQRZODUYBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  53
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  143
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2,2,6,6-Tetrakis-diisopropylamino-1,7-diaza-2λ⁵,6λ⁵-diphospha-indene-3,3a,4,5-tetracarboxylic acid tetramethyl ester 以 甲苯 为溶剂， 反应 0.33h， 以90%的产率得到2,2,6,6-Tetrakis-diisopropylamino-1,7-diaza-2λ⁵,6λ⁵-diphospha-indene-3,3,4,5-tetracarboxylic acid tetramethyl ester
  参考文献：
  名称：

  Bis(phosphino)carbodiimide: A Bis(1,3)-dipole

  摘要：

  Bis[bis(diisopropylamino)phosphino]carbodiimide (1) reacts with 1 equiv of dimethyl acetylenedicarboxylate affording the [3 + 2] cycloadduct 2 in 92% yield, showing that a phosphinocarbodiimide acts as a 1,3-dipole. Addition of a second equivalent of alkyne to 2 gives rise to the formal [2 + 7] cycloadduct 5 in 85% yield. Migration of a carbomethoxy group is observed on thermolysis of 5 at 80 degrees C, leading to a new bicyclo[4.3.0] derivative 7 in 90% yield. The X-ray diffraction study of derivatives 5 and 7 is presented. The mechanisms rationalizing the formation of 2, 5, and 7 are discussed.

  DOI：

  10.1021/jo00099a021
• 作为产物：
  描述：

  Biscarbodiimide 以 四氢呋喃 、 正戊烷 为溶剂， 反应 0.5h， 生成 2,2,6,6-Tetrakis-diisopropylamino-1,7-diaza-2λ⁵,6λ⁵-diphospha-indene-3,3a,4,5-tetracarboxylic acid tetramethyl ester
  参考文献：
  名称：

  Bis(phosphino)carbodiimide: A Bis(1,3)-dipole

  摘要：

  Bis[bis(diisopropylamino)phosphino]carbodiimide (1) reacts with 1 equiv of dimethyl acetylenedicarboxylate affording the [3 + 2] cycloadduct 2 in 92% yield, showing that a phosphinocarbodiimide acts as a 1,3-dipole. Addition of a second equivalent of alkyne to 2 gives rise to the formal [2 + 7] cycloadduct 5 in 85% yield. Migration of a carbomethoxy group is observed on thermolysis of 5 at 80 degrees C, leading to a new bicyclo[4.3.0] derivative 7 in 90% yield. The X-ray diffraction study of derivatives 5 and 7 is presented. The mechanisms rationalizing the formation of 2, 5, and 7 are discussed.

  DOI：

  10.1021/jo00099a021

文献信息

• Veneziani Guilaine, Reau Regis, Dahan Francoise, Bertrand Guy, J. Org. Chem., 59 (1994) N 20, S 5927-5929
  作者：Veneziani Guilaine, Reau Regis, Dahan Francoise, Bertrand Guy

  DOI：——

  日期：——
• Bis(phosphino)carbodiimide: A Bis(1,3)-dipole
  作者：Guilaine Veneziani、Regis Reau、Francoise Dahan、Guy Bertrand

  DOI：10.1021/jo00099a021

  日期：1994.10

  Bis[bis(diisopropylamino)phosphino]carbodiimide (1) reacts with 1 equiv of dimethyl acetylenedicarboxylate affording the [3 + 2] cycloadduct 2 in 92% yield, showing that a phosphinocarbodiimide acts as a 1,3-dipole. Addition of a second equivalent of alkyne to 2 gives rise to the formal [2 + 7] cycloadduct 5 in 85% yield. Migration of a carbomethoxy group is observed on thermolysis of 5 at 80 degrees C, leading to a new bicyclo[4.3.0] derivative 7 in 90% yield. The X-ray diffraction study of derivatives 5 and 7 is presented. The mechanisms rationalizing the formation of 2, 5, and 7 are discussed.