(R)-diethyl hydroxy(4-methoxyphenyl)methylphosphonate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-diethyl hydroxy(4-methoxyphenyl)methylphosphonate
• 英文别名: (R)-diethoxyphosphoryl-(4-methoxyphenyl)methanol
• 化学式: C₁₂H₁₉O₅P
• 分子量: 274.254
• InChiKey: JHWKOXIQEJTXHI-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 亚磷酸二乙酯 在 氯化二乙基铝 作用下， 以 四氢呋喃 为溶剂， 反应 40.0h， 生成 (S)-diethyl hydroxy(4-methoxyphenyl)methylphosphonate 、 (R)-diethyl hydroxy(4-methoxyphenyl)methylphosphonate
  参考文献：
  名称：

  双官能手性Al（III）配合物催化醛的不对称加氢羰基化反应

  摘要：

  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。

  DOI：

  10.1016/j.tet.2008.01.022

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％）。
• 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.
• Yokomatsu, Tsutomu; Yamagishi, Takehiro; Shibuya, Shiroshi, Journal of the Chemical Society. Perkin transactions I, 1997, # 10, p. 1527 - 1533
  作者：Yokomatsu, Tsutomu、Yamagishi, Takehiro、Shibuya, Shiroshi

  DOI：——

  日期：——