(S)-diethyl hydroxy(naphthalen-1-yl)methylphosphonate | 203637-18-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-diethyl hydroxy(naphthalen-1-yl)methylphosphonate
• 英文别名: (S)-diethoxyphosphoryl(naphthalen-1-yl)methanol
• CAS: 203637-18-7
• 化学式: C₁₅H₁₉O₄P
• 分子量: 294.287
• InChiKey: SBXJHSQQBUMQMD-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  1-萘甲醛 、 亚磷酸二乙酯 在 iron(III) chloride 、 (1S,2R,4R)-1-(2-hydroxy-3-methylbenzylideneamino)-7,7-dimethylbicyclo[2.2.1]heptan-2-ol 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以63%的产率得到
  参考文献：
  名称：

  Fe（III）催化手性樟脑席夫碱促进醛的对映选择性氢膦酰化

  摘要：

  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％）。

  DOI：

  10.1016/j.tetasy.2015.07.004

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。
• Manganese-proline derived new catalyst system for the enantioselective synthesis of α -hydroxyphosphonates and α -aminophosphonates
  作者：Hyun Lim、Vicklyn Datilus、Rania Teriak、Prianka Chohan、Parminder Kaur

  DOI：10.1016/j.tetlet.2017.02.088

  日期：2017.4

  A novel manganese/proline-derived catalyst system is reported for the stereoselective synthesis of α-hydroxyphosphonates and α-aminophosphonates. The reaction proceeded smoothly under mild reaction conditions with efficient reaction times. The resulting products were obtained with high yields and good enantioselectivities (up to 83% ee).

  报道了一种新颖的锰/脯氨酸衍生的催化剂体系，用于α-羟基膦酸酯和α-氨基膦酸酯的立体选择性合成。反应在温和的反应条件下以有效的反应时间顺利进行。得到的产物具有高收率和良好的对映选择性（高达83％ee）。
• 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.