diethyl 1-hydroxy-3-phenylprop-2-enyl-phosphonate | 178900-16-8

• 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 1-hydroxy-3-phenylprop-2-enyl-phosphonate
• 英文别名: (E,R)-diethyl 1-hydroxy-3-phenylallylphosphonate；(E)-diethyl 1-hydroxy-3-phenylallylphosphonate；(E,1R)-1-diethoxyphosphoryl-3-phenylprop-2-en-1-ol
• CAS: 178900-16-8
• 化学式: C₁₃H₁₉O₄P
• 分子量: 270.265
• InChiKey: VDTIGZIBQSKVCQ-OCHBPSSRSA-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

• 作为反应物：
  描述：

  diethyl 1-hydroxy-3-phenylprop-2-enyl-phosphonate 、 (S)-2-(6-甲氧基-2-萘基)丙酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以37%的产率得到(S)-2-(6-methoxy-naphthalen-2-yl)-propionic acid (R)-1-(diethoxyphosphoryl)-3-phenyl-allyl ester
  参考文献：
  名称：

  使用萘普生作为可靠的手性衍生剂，通过1 H和31 P NMR鉴定羟基和氨基膦酸二乙酯的绝对构型

  摘要：

  提出了羟基膦酸酯和氨基膦酸酯的绝对构型通过与市售萘普生的双衍生作用的分配。周围的立构碳中心的空间排列和Δδ的符号之间的相关性RS通过简单比较（R）-和（S）-萘普生酯或酰胺衍生物的1 H和31 P NMR光谱，可以确定羟基和氨基膦酸酯的绝对构型。NMR研究对结构多样的萘普生酯和羟基膦酸酯和氨基膦酸酯的酰胺进行了广泛的构象分析（理论计算，低温实验），证明了可以成功使用简化的模型。

  DOI：

  10.1021/jo062097z
• 作为产物：
  描述：

  巴豆醛 、 亚磷酸三乙酯 在 四氯化硅 、 diethyl ((R)-1-((R)-1-(diphenylphosphoryl)butan-2-yl)aziridin-2-yl)phosphonate 、 N,N-二异丙基乙胺 、 水 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以29%的产率得到
  参考文献：
  名称：

  New phosphine oxide aziridinyl phosphonates as chiral Lewis bases for the Abramov-type phosphonylation of aldehydes

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2013.04.005

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.