dibutyl 1-hydroxybutylphosphonate | 23054-89-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: dibutyl 1-hydroxybutylphosphonate
• 英文别名: (1-hydroxy-butyl)-phosphonic acid dibutyl ester；(1-Hydroxy-butyl)-phosphonsaeure-dibutylester；Dibutyl (1-hydroxybutyl)phosphonate；1-dibutoxyphosphorylbutan-1-ol
• CAS: 23054-89-9
• 化学式: C₁₂H₂₇O₄P
• 分子量: 266.318
• InChiKey: WZLQTDVXGIEMSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dibutyl 1-hydroxybutylphosphonate 、 苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (R)-1-(dibutoxyphosphoryl)butyl benzoate 、 (S)-1-(dibutoxyphosphoryl)butyl benzoate
  参考文献：
  名称：

  使用樟脑基三齿席夫碱[FeCl（SBAIB-d）] 2的铁配合物催化醛的对映选择性加氢羰基化反应

  摘要：

  AbstractAn iron(III)‐Schiff base‐catalyzed, highly enantioselective hydrophosphonylation of various aldehydes is described. Under the optimized reaction conditions, 5 mol% of the iron/camphor‐based tridentate Schiff base complex [FeCl(SBAIB‐d)]2 produces high yields (up to 99%) of α‐hydroxy phosphonates in excellent enantioselectivities (up to 99%). The merits of this catalytic system are an easily synthesizable catalyst, inexpensive starting materials, practically simple aerobic reaction conditions, and low catalyst loading (5 mol%).magnified image

  DOI：

  10.1002/adsc.201300653
• 作为产物：
  描述：

  磷酸三丁酯 在 四甲基乙二胺 、 仲丁基锂 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 3.0h， 以55%的产率得到dibutyl 1-hydroxybutylphosphonate
  参考文献：
  名称：

  The phosphonate-phosphate and phosphate-phosphonate rearrangement and their applications V. On the reaction ofs-butyllithium/TMEDA with symmetrical trialkyl phosphates

  摘要：

  1-(Tributylstannyl)hexanol ((+/-)-8) is phosphorylated to give phosphate (+/-)-9 which is then transmetallated. The organolithium intermediate (+/-)-10 isomerizes to alpha-hydroxyphosphonate (+/-)-12. Similar intermediates are also formed upon direct deprotonation of triethyl, tri-n-propyl, and tri-n-butyl phosphate, which subsequently rearrange to alpha-hydroxyphosphonates (+/-)-14a-c.

  DOI：

  10.1007/bf00807567

文献信息

• Process of preparing substituted hydroxymethylphosphonic esters
  申请人：RESEARCH CORP

  公开号：US02579810A1

  公开（公告）日：1951-12-25
• Abramow et al., Zhurnal Obshchei Khimii, 1953, vol. 23, p. 257,260; engl. Ausg. S. 269
  作者：Abramow et al.

  DOI：——

  日期：——
• Catalytic Enantioselective Hydrophosphonylation of Aldehydes Using the Iron Complex of a Camphor-Based Tridentate Schiff Base [FeCl(SBAIB-d)]₂
  作者：Ramalingam Boobalan、Chinpiao Chen

  DOI：10.1002/adsc.201300653

  日期：2013.11.25

  AbstractAn iron(III)‐Schiff base‐catalyzed, highly enantioselective hydrophosphonylation of various aldehydes is described. Under the optimized reaction conditions, 5 mol% of the iron/camphor‐based tridentate Schiff base complex [FeCl(SBAIB‐d)]2 produces high yields (up to 99%) of α‐hydroxy phosphonates in excellent enantioselectivities (up to 99%). The merits of this catalytic system are an easily synthesizable catalyst, inexpensive starting materials, practically simple aerobic reaction conditions, and low catalyst loading (5 mol%).magnified image
• The phosphonate-phosphate and phosphate-phosphonate rearrangement and their applications V. On the reaction ofs-butyllithium/TMEDA with symmetrical trialkyl phosphates
  作者：F. Hammerschmidt、S. Schmidt

  DOI：10.1007/bf00807567

  日期：1997.11

  1-(Tributylstannyl)hexanol ((+/-)-8) is phosphorylated to give phosphate (+/-)-9 which is then transmetallated. The organolithium intermediate (+/-)-10 isomerizes to alpha-hydroxyphosphonate (+/-)-12. Similar intermediates are also formed upon direct deprotonation of triethyl, tri-n-propyl, and tri-n-butyl phosphate, which subsequently rearrange to alpha-hydroxyphosphonates (+/-)-14a-c.