diethyl (S)-1-hydroxy-3-phenyl-2(E)-propenylphosphonate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: diethyl (S)-1-hydroxy-3-phenyl-2(E)-propenylphosphonate
• 英文别名: diethyl 1-hydroxy-3-phenylprop-2-enyl-phosphonate；(E,S)-diethyl 1-hydroxy-3-phenylallylphosphonate；(E)-diethyl 1-hydroxy-3-phenylallylphosphonate；(E,1S)-1-diethoxyphosphoryl-3-phenylprop-2-en-1-ol
• 化学式: C₁₃H₁₉O₄P
• 分子量: 270.265
• InChiKey: VDTIGZIBQSKVCQ-NHAQELONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  diethyl 1-acetyloxy-3-phenyl-2(E)-propenylphosphonate 在 potassium osmate(VI) 甲基磺酰胺 、 AD-mix-β 、 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 8.0h， 生成 diethyl (S)-1-hydroxy-3-phenyl-2(E)-propenylphosphonate
  参考文献：
  名称：

  Asymmetric dihydroxylation of 1-acyloxy-2(E)-alkenylphosphonates with AD-mix reagents. Effects of 1-acyloxy functional groups on the asymmetric dihydroxylation

  摘要：

  Asymmetric dihydroxylation (AD) of a racemic mixture of 1-acyloxy-2(E)-alkenylphosphonates with AD-mix-alpha or -beta reagents was examined. The kinetic rate of dihydroxylation was highly dependent upon the configuration of the 1-acyloxy functional group as well as the nature of substituents at the 3-position. ?he reaction of a racemic mixture of diethyl (E)-3-phenyl-1-acetyloxy-2-propenylphosphonate with an AD-mix-beta reagent preferentially dihydroxylated the R-enantiomer to leave an unreacted S-enantiomer of high enantiomeric purity. Double diastereoselection of the resolved diethyl 3-phenyl-1-acetyloxy-2(E)-propenylphosphonate in dihydroxylation was also examined. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10342-8

文献信息

• Asymmetric hydrophosphonylation of aldehydes catalyzed by bifunctional chiral Al(III) complexes
  作者：Shaohua Gou、Xin Zhou、Jun Wang、Xiaohua Liu、Xiaoming Feng

  DOI：10.1016/j.tet.2008.01.022

  日期：2008.3

  effective enantioselective hydrophosphonylation of aldehydes. A variety of aromatic, heteroaromatic, condensed-ring, α,β-unsaturated, and aliphatic aldehydes were found to be suitable substrates for the reaction, and the desired α-hydroxy phosphonate were obtained in good to excellent yields (up to 99%) with moderate to good enantioselectivities (up to 87% ee) under mild conditions (at 0 °C). A possible

  一种新的手性双官能的Al（Ⅲ）配合物的BINOL衍生物，其中载有叔在BINOL的3,3'-位置-胺，已发展为醛的对映选择性有效hydrophosphonylation。发现各种芳族，杂芳族，稠环，α，β-不饱和和脂族醛是反应的合适底物，并且以良好或优异的收率（高达99％）获得了所需的α-羟基膦酸酯。在温和条件下（0°C）具有中等至良好的对映选择性（高达87％ee）。根据实验结果提出了可能的催化循环。
• Bis(oxazoline)-copper catalyzed enantioselective hydrophosphonylation of aldehydes
  作者：Tao Deng、Chun Cai

  DOI：10.1039/c4ra03269a

  日期：——

  A highly enantioselective copper-catalyzed hydrophosphonylation of aldehydes in the presence of bis(oxazoline) ligand is presented. The reaction proceeded smoothly under mild conditions. The resulting α-hydroxyphosphonates were obtained with high yields as well as enantioselectivities (up to 98% ee).

  提出了在双（恶唑啉）配体存在下醛的高度对映选择性的铜催化的羰基膦酰化。反应在温和的条件下顺利进行。以高收率和对映选择性（高达98％ee）获得所得的α-羟基膦酸酯。
• Synthesis of aryl group-modified DIOP dioxides (Ar-DIOPOs) and their application as modular Lewis base catalysts
  作者：Yusuke Ohmaru、Norimasa Sato、Makoto Mizutani、Shunsuke Kotani、Masaharu Sugiura、Makoto Nakajima

  DOI：10.1039/c2ob25338k

  日期：——

  transformations using chlorosilane reagents. The p-tolyl-substituted DIOPO (p-tolyl-DIOPO) was most effective for the reductive aldol reaction of chalcone and aldehydes with trichlorosilane, whereas the 2,8-dimethylphenoxaphosphine-derived DIOPO (DMPP-DIOPO) afforded the best enantioselectivity for the phosphonylation of conjugated aldehydes and the chlorinative aldol reaction of an ynone and benzaldehyde.

  用LHMDS处理光学纯的酒石酸衍生的二碘化物和各种仲氧化膦，可提供相应的经芳基改性的DIOP二氧化物（Ar-DIOPO）。使用氯硅烷试剂研究了Ar-DIOPO作为Lewis碱催化剂的活性，进行了几次不对称转化。的p -甲苯基-取代的DIOPO（p甲苯基- DIOPO）是最有效的还原醛醇缩合反应查尔酮 和醛与 三氯硅烷，而2,8-二甲基苯氧杂膦衍生的DIOPO（DMPP-DIOPO）提供了最佳的对映体选择性，使共轭醛的膦酰化反应和炔酮和乙炔的氯代醛醇缩合反应。 苯甲醛。
• Chiral N,N′-dioxide-Yb(III) complexes catalyzed enantioselective hydrophosphonylation of aldehydes
  作者：Weiliang Chen、Yonghai Hui、Xin Zhou、Jun Jiang、Yunfei Cai、Xiaohua Liu、Lili Lin、Xiaoming Feng

  DOI：10.1016/j.tetlet.2010.05.137

  日期：2010.8

  Chiral N,N'-dioxide-Ytterbium(III) complexes promoted the asymmetric addition of diethyl phosphate to aldehydes, giving the corresponding products with good yields and enantioselectivities. The addition of pyridine favored both reactivity and enantioselectivity. A possible catalytic cycle was proposed to explain the mechanism of the asymmetric hydrophosphonylation of aldehydes. (C) 2010 Elsevier Ltd. All rights reserved.
• New phosphine oxide aziridinyl phosphonates as chiral Lewis bases for the Abramov-type phosphonylation of aldehydes
  作者：Özdemir Dogan、Muhammet Isci、Muhittin Aygun

  DOI：10.1016/j.tetasy.2013.04.005

  日期：2013.5

  A series of Lewis bases were screened for Abramov-type phosphine additions to aldehydes. A novel phosphine oxide aziridinyl phosphonate POAP-A was found to be better than the others in forming the product in 96% yield and with 42% ee. The absolute configuration of the newly synthesized POAP Lewis bases was determined by single-crystal X-ray analysis. (C) 2013 Elsevier Ltd. All rights reserved.