1-oxo-1-isopropyl phospholane | 133471-41-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 金属杂环化合物
• 英文名称: 1-oxo-1-isopropyl phospholane
• 英文别名: Isopropyl phospholanate；1-Propan-2-yloxy-1lambda5-phospholane 1-oxide；1-propan-2-yloxy-1λ5-phospholane 1-oxide
• CAS: 133471-41-7
• 化学式: C₇H₁₅O₂P
• 分子量: 162.169
• InChiKey: QQOXZFJEOSDHEW-UHFFFAOYSA-N

物化性质

• 沸点：
  140 °C(Press: 0.2 Torr)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-oxo-1-isopropyl phospholane 在 Li-tetramethylpiperidide 作用下， 反应 6.0h， 生成 meso-Isopropyl cis-2,5-dibenzylphospholanate
  参考文献：
  名称：

  Preparation, alkylation reactions, and conformational analysis of esters of phospholanic acid. Preparation and reactivity of (2S*,5S*)-1,2,5-tribenzyl-1-oxophospholane

  摘要：

  Optimum conditions for the reaction of 1,4-butanediyldimagnesium dibromide and alkyl phosphorodichloridates are described. The general geometric requirements of the cyclization reaction transition state are discussed. Alkylation reactions of phospholanate esters 2b and 2c are reported. Conformational analysis of various phospholanate esters is discussed in terms of 3J(PC) and 3J(PH) data, NOE experiments, and crystal structures of related phospholane derivatives. trans-2,5-Dibenzyl phosphinate esters 15b and 15c were converted to (2S*,5S*)-1,2,5-tribenzyl-1-oxophospholane 18 by reductive alkylation. Phosphine oxide 18 was shown to participate in an olefination reaction with 4-tert-butylcyclohexanone.

  DOI：

  10.1021/jo00009a039
• 作为产物：
  描述：

  1,4-二溴丁烷 、 isopropyl phosphorodichloridate 在 碘 magnesium 、 1,2-二溴乙烷 作用下， 生成 1-oxo-1-isopropyl phospholane
  参考文献：
  名称：

  Preparation, alkylation reactions, and conformational analysis of esters of phospholanic acid. Preparation and reactivity of (2S*,5S*)-1,2,5-tribenzyl-1-oxophospholane

  摘要：

  Optimum conditions for the reaction of 1,4-butanediyldimagnesium dibromide and alkyl phosphorodichloridates are described. The general geometric requirements of the cyclization reaction transition state are discussed. Alkylation reactions of phospholanate esters 2b and 2c are reported. Conformational analysis of various phospholanate esters is discussed in terms of 3J(PC) and 3J(PH) data, NOE experiments, and crystal structures of related phospholane derivatives. trans-2,5-Dibenzyl phosphinate esters 15b and 15c were converted to (2S*,5S*)-1,2,5-tribenzyl-1-oxophospholane 18 by reductive alkylation. Phosphine oxide 18 was shown to participate in an olefination reaction with 4-tert-butylcyclohexanone.

  DOI：

  10.1021/jo00009a039

文献信息

• NOVEL GLUCOKINASE ACTIVATORS AND METHODS OF USING SAME
  申请人：Ryono Denis E.

  公开号：US20080009465A1

  公开（公告）日：2008-01-10

  Compounds are provided which are phosphonate and phosphinate activators and thus are useful in treating diabetes and related diseases and have the structure wherein is a heteroaryl ring; R 4 is —(CH 2 ) n -Z-(CH 2 ) m —PO(OR 7 )(OR 8 ), —(CH 2 ) n Z-(CH 2 ) m —PO(OR 7 )R g , —(CH 2 ) n -Z-(CH 2 ) m —OPO(OR 7 )R g , —(CH 2 ) n Z—(CH 2 ) m —OPO(R 9 )(R 10 ), or —(CH 2 ) n Z—(CH 2 ) m —PO(R 9 )(R 10 ); R 5 and R 6 are independently selected from H, alkyl and halogen; Y is R 7 (CH 2 ) s or is absent; and X, n, Z, m, R 4 , R 5 , R 6 , R 7 , and s are as defined herein; or a pharmaceutically acceptable salt thereof. A method for treating diabetes and related diseases employing the above compounds is also provided.

  提供了磷酸酯和磷酸酯激活剂，因此在治疗糖尿病和相关疾病方面非常有用，并具有以下结构： 其中 是杂环芳基环； R 4 为—(CH 2 ) n -Z-(CH 2 ) m —PO(OR 7 )(OR 8 )、—(CH 2 ) n Z-(CH 2 ) m —PO(OR 7 )R g 、—(CH 2 ) n -Z-(CH 2 ) m —OPO(OR 7 )R g 、—(CH 2 ) n Z—(CH 2 ) m —OPO(R 9 )(R 10) 或—(CH 2 ) n Z—(CH 2 ) m —PO(R 9 )(R 10) ； R 5 和R 6 分别选择自H、烷基和卤素； Y为R 7 (CH 2 ) s 或不存在；以及 X、n、Z、m、R 4 、R 5 、R 6 、R 7 和s如本文所定义；或其药用盐。 还提供了一种利用上述化合物治疗糖尿病和相关疾病的方法。
• MONO- AND DIALKYLATION OF ISOPROPYL PHOSPHINATE-A SIMPLE PREPARATION OF ALKYLPHOSPHINATE ESTERS¹
  作者：Michael J. Gallagher、Millagahamada G. Ranasinghe、Ian D. Jenkins

  DOI：10.1080/10426509608037971

  日期：1996.8.1

  Abstract Base-catalysed alkylation of isopropyl phosphinate with primary alkyl halides under mild conditions affords the corresponding alkyl phosphinate esters in fair to excellent yields.

  摘要 在温和条件下，用伯烷基卤化物碱催化亚膦酸异丙酯烷基化反应，得到相应的亚膦酸烷基酯，产率一般到极好。
• POLNIASZEK, RICHARD P.;FOSTER, ALVIE L., J. ORG. CHEM., 56,(1991) N, C. 3137-3146
  作者：POLNIASZEK, RICHARD P.、FOSTER, ALVIE L.

  DOI：——

  日期：——
• US7910747B2
  申请人：——

  公开号：US7910747B2

  公开（公告）日：2011-03-22
• US8153677B2
  申请人：——

  公开号：US8153677B2

  公开（公告）日：2012-04-10