1-Methylphosphorinan | 39763-50-3

• 分子结构分类: 有机化合物 - 有机磷化合物 - 有机膦及其衍生物
• 英文名称: 1-Methylphosphorinan
• 英文别名: 1-methylphosphinane；1-methyl-phosphinane；p-methylcyclopentamethylenephosphine；1-Methyl-phosphorinan
• CAS: 39763-50-3
• 化学式: C₆H₁₃P
• 分子量: 116.143
• InChiKey: WKJBDCNEMDIONX-UHFFFAOYSA-N

物化性质

• 沸点：
  145-147 °C

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-Methylphosphorinan 在 溴 作用下， 以 二氯甲烷 为溶剂， 生成 1-bromo-1-methyl-phosphinanium; bromide
  参考文献：
  名称：

  The structure in solution of the halogen adducts of phosphines and arsines

  摘要：

  DOI：

  10.1021/jo00428a010
• 作为产物：
  描述：

  1-phenylphosphinane 在 sodium hydroxide 、 苯硅烷 作用下， 生成 1-Methylphosphorinan
  参考文献：
  名称：

  Alkaline cleavage reactions of tetraalkylphosphonium salts

  摘要：

  DOI：

  10.1021/ja00782a035

文献信息

• Catalytic Preparation of Cyclic Carboxylic Esters
  申请人：Spindler Felix

  公开号：US20090275761A1

  公开（公告）日：2009-11-05

  Preparation of cyclic esters by hydrogenation of a carbonyl group in at least one anhydride radical —C(O)—O—C(O)— of a cyclic dicarboxylic or polycarboxylic anhydride by means of hydrogen in the presence of a homogeneous noble metal catalyst, characterized in that the hydrogenation is carried out in a homogeneous reaction mixture using an iridium catalyst. The cyclic esters are obtained in good chemical and optical yields when prochiral anhydrides are used together with chiral iridium catalysts.

  通过在至少一个环状二羧酸酐基团—C(O)—O—C(O)—中的羰基团上加氢来制备环酯，所述环状二羧酸酐为环状二羧酸酐或多羧酸酐，通过在均相贵金属催化剂存在下使用氢气，在均相反应混合物中使用铱催化剂进行氢化反应。当使用外消旋酸酐与手性铱催化剂一起时，可以获得良好的化学和光学产率。
• [EN] BIDENTATE CHIRAL LIGANDS FOR USE IN CATALYTIC ASYMMETRIC ADDITION REACTIONS<br/>[FR] LIGANDS CHIRAUX BIDENTATES UTILISABLES DANS DES RÉACTIONS D'ADDITION CATALYTIQUES ASYMÉTRIQUES
  申请人：SOLVIAS AG

  公开号：WO2009065784A1

  公开（公告）日：2009-05-28

  Compounds of the formula (I), in the form of mixtures comprising predominantly one diastereomer or in the form of pure diastereomers, Z1-Q-P*R0R1 (I) in which Z1 is a C-bonded, secondary phosphine group -P(R)2; in which R is in each case independently hydrocarbon radicals or heterohydrocarbon radicals, or Z1 is the -P*R0R1 group; Q is a bivalent, achiral, aromatic base skeleton, a bivalent, achiral ferrocene base skeleton, an optionally substituted bivalent cycloalkane or heterocycloalkane skeleton, or a C1-C4-alkylene skeleton, and in which base skeletons a secondary phosphine group Z1 is bonded directly to a carbon atom, or, in the case of cyclic base skeletons, directly to a carbon atom or via a C1-C4-alkylene group, and in which base skeletons a P-chiral group -P*R0R1 is bonded directly to a carbon atom, or, in the case of cyclic base skeletons, directly to a carbon atom or via a C1-C4-alkylene group to a carbon atom such that the phosphorus atoms are linked via 1 to 7 atoms of a carbon chain optionally interrupted by heteroatoms from the group of O, S, N, Fe or Si; P* is a chiral phosphorus atom; R0 is methyl or hydroxyl, and R0 is methyl when Z1 is the -P*R0R1 group; and R1 is a C-bonded optically enriched or optically pure chiral, mono- or polycyclic, nonaromatic hydrocarbon or heterohydrocarbon radical which has 3 to 12 ring atoms and 1 to 4 rings and which has a stereogenic carbon atom at least in the α position to the P-C bond; Metal complexes of these ligands are homogeneous catalysts for asymmetric addition reactions, particularly hydrogenations.

  化合物的公式（I）的形式，以主要包含一种对映异构体的混合物形式或纯对映异构体的形式，Z1-Q-P*R0R1（I），其中Z1是C-键合的次磷酸基团-P（R）2；其中R分别是烃基或杂烃基，或Z1是-P*R0R1基团；Q是二价的、不对映的、芳香基骨架，二价的、不对映的二茂铁基骨架，一个可选择取代的二价环烷烃或杂环烷烃骨架，或一个C1-C4-烷基骨架，并且在这些基骨架中，次磷酸基团Z1直接键合到一个碳原子，或者在环状基骨架的情况下，直接键合到一个碳原子或通过一个C1-C4-烷基团，以及在这些基骨架中，一个P-手性基团-P*R0R1直接键合到一个碳原子，或者在环状基骨架的情况下，直接键合到一个碳原子或通过一个C1-C4-烷基团到一个碳原子，以使磷原子通过1到7个碳链原子连接，这些碳链原子可以通过来自O、S、N、Fe或Si的杂原子间断连接；P*是一个手性磷原子；R0是甲基或羟基，当Z1是-P*R0R1基团时，R0是甲基；R1是一个C-键合的光学富集或光学纯的手性、单环或多环、非芳香烃基或杂烃基，具有3到12个环原子和1到4个环，并且至少在P-C键的α位置具有一个立体异构碳原子；这些配体的金属络合物是用于不对称加成反应的均相催化剂，特别是氢化反应。
• Asymmetric Catalytic Hydrogenation of Prochiral Ketones and Aldehydes
  申请人：Spindler Felix

  公开号：US20090105481A1

  公开（公告）日：2009-04-23

  Process for stereoselective hydrogenation by reacting racemic aldehydes or ketones having a stereogenic carbon atom in the position relative to the C(O) group and containing the structural element —(O)C—C—CH— by means of hydrogen in the presence of a base and a ruthenium complex containing a bidentate ligand having coordinating P and N atoms, a monophosphine ligand and anionic and/or uncharged ligands as homogeneous catalyst, with the charge being balanced by one or two monovalent acid anions or a divalent acid anion when uncharged ligands are present.

  通过在碱和含有具有配位P和N原子的双齿配体、单膦配体和阴离子和/或无电荷配体的钌配合物的存在下，通过氢气作用于相对于C(O)基团位置上含有立体异构碳原子和结构元素—(O)C—C—CH—的外消旋醛或酮，进行立体选择性加氢的过程，其中当存在无电荷配体时，通过一个或两个一价酸阳离子或二价酸阴离子平衡电荷。
• The First Flights of a Molecular Shuttle Transporting Elements: Easy One-pot Formation of Organic Cyclic Arsanes, Stibanes and Bismutanes
  作者：Graziano Baccolini、Carla Boga、Marzia Mazzacurati、Gabriele Micheletti

  DOI：10.1002/chem.200802007

  日期：2009.1.5

  Maiden voyage: New arsenic‐, antimony‐ and bismuth‐donor reagents (1 b–d) are used in a one‐pot synthesis of cyclic arsanes, stibanes and bismutanes through a procedure in which the simultaneous formation of three CAs, CSb or CBi bonds is achieved. At the end of the reaction, the element‐donor reagent can be easily re‐formed “in situ” and recycled, as in a catalytic process.

  处女航次：一种新的砷，锑和铋供体试剂（1 b – d）通过一种同时合成三个C rs As，C的方法，用于一锅合成环状a烷，二苯乙烯和双变烷获得Sb或CBi键。在反应结束时，可以像在催化过程中一样轻松地“原位”重组元素供体试剂并回收利用。
• Ferrocenyl Ligands For Homogeneous, Enantioselective Hydrogenation Catalysts
  申请人：Lotz Matthias

  公开号：US20080287698A1

  公开（公告）日：2008-11-20

  Compounds of the formula (I) or (I′), where R 1 is a hydrogen atom or C 1 -C 4 -alkyl and R′ 1 is C 1 -C 4 -alkyl; X 1 and X 2 are each, independently of one another, a secondary phosphine group; R 2 is hydrogen, R 01 R 02 R 03 Si—, C 1 -C 18 acyl substituted by halogen, hydroxy, C 1 -C 8 -alkoxy or R 04 R 05 N—, -or R 06 —X 01 —C(O)—; R 01 , R 02 and R 03 are each, independently of one another, C 1 -C 12 -alkyl, unsubstituted or C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy-substituted C 6 -C 10 -aryl or C 7 -C 12 -aralkyl; R 04 and R 05 are each, independently of one another, hydrogen, C 1 -C 12 -alkyl, C 3 -C 8 -cycloalkyl, C 6 -C 10 -aryl or C 7 -C 12 -aralkyl, or R 04 and R 05 together are trimethylene, tetramethylene, pentamethylene or 3-oxapcntylene; R 06 is C 1 -C 18 -alkyl, unsubstituted or C 1 -C 4 -alkyl- or C 1 -C 4 -alkoxy-substituted C 3 -C 8 -cycloalkyl, C 6 -C 10 -aryl or C 7 -C 12 -aralkyl; X 01 is —O— or —NH—; T is C 6 -C 20 -arylene; v is 0 or an integer from 1 to 4; and * denotes a mixture of racemic or enantiomerically pure diastereomers or pure racemic or enantiomerically diastereomers, are excellent chiral ligands for metal complexes as enantioselective catalysts for the hydrogenation of prochiral organic compounds.

  式(I)或(I′)的化合物，其中R1是氢原子或C1-C4-烷基，R′1是C1-C4-烷基；X1和X2分别是次磷酸基团；R2是氢，R01R02R03Si—，C1-C18酰基取代的卤素、羟基、C1-C8烷氧基或R04R05N—，或R06—X01—C(O)—；R01、R02和R03分别是C1-C12烷基、未取代或C1-C4烷基或C1-C4烷氧基取代的C6-C10芳基或C7-C12芳基烷基；R04和R05分别是氢、C1-C12烷基、C3-C8环烷基、C6-C10芳基或C7-C12芳基烷基，或者R04和R05一起是三亚甲基、四亚甲基、五亚甲基或3-氧代戊亚甲基；R06是C1-C18烷基，未取代或C1-C4烷基或C1-C4烷氧基取代的C3-C8环烷基、C6-C10芳基或C7-C12芳基烷基；X01是—O—或—NH—；T是C6-C20芳基；v是0或1到4的整数；*表示混合的外消旋或对映纯二对映体或纯外消旋或对映纯二对映体，对于金属络合物作为催化剂，对非手性有机化合物的氢化反应具有优异的手性配体。

表征谱图