(S)-bis(2,2,2-trifluoroethoxy)phosphoryl-phenylmethanol | 1045892-61-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: (S)-bis(2,2,2-trifluoroethoxy)phosphoryl-phenylmethanol
• CAS: 1045892-61-2
• 化学式: C₁₁H₁₁F₆O₄P
• 分子量: 352.17
• InChiKey: NBJOQOVWKAMLDS-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (S)-bis(2,2,2-trifluoroethoxy)phosphoryl-phenylmethanol 在 水 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以96%的产率得到(-)-(S)-1-phenyl-1-hydroxymethylphosphonic acid
  参考文献：
  名称：

  Catalytic Enantioselective Pudovik Reaction of Aldehydes and Aldimines with Tethered Bis(8-quinolinato) (TBOx) Aluminum Complex

  摘要：

  New chiral tethered bis(8-quinolinolato) (TBOx) aluminum(III) complexes effectively catalyze the addition of phosphites to aldehydes and aldimines to give enantioenriched alpha-hydroxy and a-amino phosphonates in high yields and enantioselectivities with unprecedented reactivity (TON = 100 as high as 200). The catalyst is optimized with the low catalyst loading of 0.5 - 1.0 mol %. The modular synthesis of the catalyst allows for potential to tune the reaction for maximum catalytic activity. To date there are few examples with broad substrate scopes that can catalyze both aldehydes and aldimines with such high selectivity and no reports utilizing such low catalyst loading.

  DOI：

  10.1021/ja803859p
• 作为产物：
  描述：

  bis(2,2,2-trifluoroethyl)phosphite 、 苯甲醛 在 C₆₄H₆₀AlClN₂O₂ 作用下， 以 正己烷 为溶剂， 反应 0.08h， 以96%的产率得到(S)-bis(2,2,2-trifluoroethoxy)phosphoryl-phenylmethanol
  参考文献：
  名称：

  Catalytic Enantioselective Pudovik Reaction of Aldehydes and Aldimines with Tethered Bis(8-quinolinato) (TBOx) Aluminum Complex

  摘要：

  New chiral tethered bis(8-quinolinolato) (TBOx) aluminum(III) complexes effectively catalyze the addition of phosphites to aldehydes and aldimines to give enantioenriched alpha-hydroxy and a-amino phosphonates in high yields and enantioselectivities with unprecedented reactivity (TON = 100 as high as 200). The catalyst is optimized with the low catalyst loading of 0.5 - 1.0 mol %. The modular synthesis of the catalyst allows for potential to tune the reaction for maximum catalytic activity. To date there are few examples with broad substrate scopes that can catalyze both aldehydes and aldimines with such high selectivity and no reports utilizing such low catalyst loading.

  DOI：

  10.1021/ja803859p

文献信息

• 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