(R)-dibutyl hydroxy(phenyl)methylphosphonate

• 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: (R)-dibutyl hydroxy(phenyl)methylphosphonate
• 英文别名: (R)-dibutoxyphosphoryl(phenyl)methanol
• 化学式: C₁₅H₂₅O₄P
• 分子量: 300.335
• InChiKey: WXXIFQYVXITZBX-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  三丁基,三丁酯 在 C₃₆H₄₆Cl₂Fe₂N₂O₄ 、 水 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 (R)-dibutyl hydroxy(phenyl)methylphosphonate
  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

文献信息

• Fe(III) catalyzed enantioselective hydrophosphonylation of aldehydes promoted by chiral camphor Schiff bases
  作者：Feng Xu、Yanpeng Liu、Jingxuan Tu、Chao Lei、Gaoqiang Li

  DOI：10.1016/j.tetasy.2015.07.004

  日期：2015.9

  Five novel chiral camphor Schiff bases were designed. Schiff base L3 showed high efficiency in Fe(III)-catalyzed asymmetric hydrophosphonylations of aldehydes, giving the corresponding products in high yields (up to 91%) along with moderate to good enantioselectivities (up to 82%).

  设计了五个新颖的手性樟脑席夫碱。Schiff碱L 3在Fe（III）催化的醛的不对称氢膦酰化反应中显示出很高的效率，从而以高收率（高达91％）提供了相应的产物，同时具有中等至良好的对映选择性（高达82％）。
• 1,1′-Dibenzyl-bis-(triazolyl)diphenylphosphine dioxide: a new efficient organocatalyst for silicon tetrachloride-mediated enantioselective Abramov-type phosphonylation of aldehydes with trialkyl phosphites
  作者：Nicolas Sevrain、Jean-Noël Volle、Jean-Luc Pirat、Tahar Ayad、David Virieux

  DOI：10.1039/c7ra10919a

  日期：——

  Asymmetric phosphonylation of aldehydes with trialkyl phosphites using a combination of SiCl4 and a novel 1,1′-dibenzyl-bis-(triazolyl)diphenylphosphine dioxide organocatalyst has been developed. This protocol provides the corresponding α-hydroxyphosphonates with a broad range of functional groups and substitution patterns in excellent yields and good selectivities.

  已经开发了使用SiCl 4和新型的1,1'-二苄基-双-（三唑基）二苯基膦二氧化膦有机催化剂组合的醛与亚磷酸三烷基酯的不对称膦酰化反应。该方案以优异的产率和良好的选择性为相应的α-羟基膦酸酯提供了广泛的官能团和取代方式。
• Catalytic Asymmetric Synthesis of α-Hydroxy Phosphonates Using the Al−Li−BINOL Complex
  作者：Takayoshi Arai、Masahiro Bougauchi、Hiroaki Sasai、Masakatsu Shibasaki

  DOI：10.1021/jo960180o

  日期：1996.1.1
• 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