N-phthalimide phenylalanyl phosphonate diethyl ester | 251983-07-0

• 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: N-phthalimide phenylalanyl phosphonate diethyl ester
• 英文别名: 2-[(2S)-1-diethoxyphosphoryl-1-oxo-3-phenylpropan-2-yl]isoindole-1,3-dione
• CAS: 251983-07-0
• 化学式: C₂₁H₂₂NO₆P
• 分子量: 415.383
• InChiKey: RHUCAZBTNZZLMF-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  90
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-phthalimide phenylalanyl phosphonate diethyl ester 在 盐酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (S)-diethyl (1-diazo-2-(1,3-dioxoisoindolin-2-yl)-3-phenylpropyl)phosphonate
  参考文献：
  名称：

  Trifluoroborane-Catalyzed C–H Functionalization/S–H Insertion Reaction: Construction of N,S-Acetal Quaternary Centers

  摘要：

  三氟硼烷催化的α-重氮磷酸酯与硫醇的C-H官能化/S-H插入反应已经被开发出来。已经提出了一个合理的反应机理来理解这个复合反应。这个过程以中等到良好的产率和化学选择性提供了直接访问含有季铵中心的N,S-缩醛。

  DOI：

  10.1055/s-0034-1380384
• 作为产物：
  描述：

  L-苯丙氨酸 在 氯化亚砜 、 溶剂黄146 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 N-phthalimide phenylalanyl phosphonate diethyl ester
  参考文献：
  名称：

  Trifluoroborane-Catalyzed C–H Functionalization/S–H Insertion Reaction: Construction of N,S-Acetal Quaternary Centers

  摘要：

  三氟硼烷催化的α-重氮磷酸酯与硫醇的C-H官能化/S-H插入反应已经被开发出来。已经提出了一个合理的反应机理来理解这个复合反应。这个过程以中等到良好的产率和化学选择性提供了直接访问含有季铵中心的N,S-缩醛。

  DOI：

  10.1055/s-0034-1380384

文献信息

• Uncatalyzed Addition of TMSCN to Acylphosphonates
  作者：Ayhan Demir、Ömer Reis、Metin Kayalar、Serkan Eymur、Barbaros Reis

  DOI：10.1055/s-2006-951558

  日期：——

  The cyanosilylations of various alkyl- and arylphosphonates under comparatively mild conditions furnished the trimethylsilyloxycyanophosphonates in high yield. The addition to ketophosphonate functions works without the influence of a catalyst.

  在相对温和的条件下，对各种烷基和芳基磷酸酯进行氰基硅醇化反应，得到了高产率的三甲基硅氧基氰基磷酸酯。对酮磷酸酯功能的加成在没有催化剂的影响下进行。
• Diastereoselective synthesis of β-amino-α-hydroxy phosphonates via oxazaborolidine catalyzed reduction of β-phthalimido-α-keto phosphonates
  作者：Achille Barco、Simonetta Benetti、Paola Bergamini、Carmela De Risi、Paolo Marchetti、Gian P. Pollini、Vinicio Zanirato

  DOI：10.1016/s0040-4039(99)01573-7

  日期：1999.10

  Reduction of β-phthalimido-α-keto phosphonates, obtained through an Arbuzov reaction between the appropriate acid chloride and triethyl phosphite, with boranes and oxazaborolidine as catalyst, afforded β-phthalimido-α-hydroxy phosphonates in good yields and high diastereoselectivity. Deprotection of the amino group gave the title compounds.

  通过适当的酰氯和亚磷酸三乙酯之间的Arbuzov反应，以硼烷和恶唑硼烷为催化剂，还原β-邻苯二甲酰亚胺基-α-羟基膦酸酯，可提供高收率和高非对映选择性的β-邻苯二甲酰亚胺基-α-羟基膦酸酯。氨基的脱保护得到标题化合物。
• 1,2-Hydride Migration in Dialkyl α-Diazophosphonates Catalyzed by [Cu(MeCN)4]PF6: A Novel Approach to β-Amino (E)-Enylphosphonates
  作者：Zhiwei Miao、Haihong Ge、Shuang Liu、Yan Cai、Yuchao Sun

  DOI：10.1055/s-0035-1560373

  日期：——

  The regiospecific and stereoselective 1,2-migration reaction of dialkyl alpha-diazophosphonates for the synthesis of beta-amino (E)-enylphosphonates is developed utilizing tetrakis(acetonitrile)copper(I) hexafluorophosphate [Cu(MeCN)(4)PF6] as the catalyst and N,N-dimethylformamide as an additive. A possible mechanism for the 1,2-migration reaction involving a metal carbene is presented. An investigation on the E/Z isomer selectivity of this process demonstrates that steric factors play an important role on the outcome. This process provides a straightforward access to beta-amino (E)-enylphosphonates in moderate to good yields.
• Unexpected Stereoselective Synthesis of (<i>Z</i>)-β-Alkenyl Substituted β-Amino Phosphonates through β,γ-Dihydrogen Shift Reaction Catalyzed by a Copper(I) Complex and Iodine [Cu(MeCN)₄]PF₆/I₂
  作者：Yan Cai、Hairong Lyu、Chengbin Yu、Zhiwei Miao

  DOI：10.1002/adsc.201300838

  日期：2014.2.10

  AbstractA series of dialkyl α‐diazophosphonates has been prepared from natural amino acids. The diazo decomposition of these diazophosphonate compounds with tetrakis(acetonitrile)copper(I) hexafluorophosphate/iodine, [Cu(MeCN)4]PF6/I2, as catalyst has been investigated. It was found that the diazo decomposition of dialkyl α‐diazophosphonates gave a mixture of β,γ‐dihydrogen shift and 1,2‐hydride migration products and afforded β‐alkenyl‐substituted β‐amino phosphonates with the Z configuration. The mechanism of this novel diazo decomposition process was discussed.magnified image
• α-AMINO ACID DERIVED BISPHOSPHONATES. SYNTHESIS AND ANTI-RESORFTIVE ACTIVITY
  作者：Dana M. Mizrahi、Trevor Waner、Yoffi Segall

  DOI：10.1080/10426500108045257

  日期：2001.8

  Eleven new bisphosphonates were prepared from naturally-occurring I-amino acids. The synthesis required special attention to amino and side-chain protections. The novel compounds were tested in TPTX (thyroparathyroidectomized) rats against arotinoid-induced hypercalcemia and were compared to alendronate. Most of the compounds showed moderate to no anti-resorptive activity. Two compounds were more active than clodronate, but less than alendronate. Limited SAR conclusions were drawn.