(2S,1'R/S)-Ethyl-2-(1'-ethoxyethoxy)propanoate | 184110-35-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,1'R/S)-Ethyl-2-(1'-ethoxyethoxy)propanoate
• 英文别名: ethyl (S)-2-(1-ethoxyethoxy)propanate；ethyl (2S)-2-(1-ethoxyethoxy)propanoate
• CAS: 184110-35-8
• 化学式: C₉H₁₈O₄
• 分子量: 190.24
• InChiKey: PDPLXOZIQCYODY-JAMMHHFISA-N

物化性质

• 沸点：
  230.5±15.0 °C(Predicted)
• 密度：
  0.980±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,1'R/S)-Ethyl-2-(1'-ethoxyethoxy)propanoate 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 (S)-1-tosyl-2-(1-ethoxyethoxy)propane
  参考文献：
  名称：

  手性，对映体纯的硫二甘醇和二甘醇的新型合成

  摘要：

  天然α-羟基酸已经按照O-保护，还原，O-活化，硫醚和醚形成和脱保护的顺序转化为手性，非外消旋的β，β'-二羟基硫醚1a，1b和醚1c。总体收率极好（75％）。为了合成相应的衍生自扁桃酸1，3-二氧戊环衍生物7的二羟基醚1d。

  DOI：

  10.1016/s0957-4166(98)00224-9
• 作为产物：
  描述：

  L(-)-乳酸乙酯 生成 (2S,1'R/S)-Ethyl-2-(1'-ethoxyethoxy)propanoate
  参考文献：
  名称：

  Synthesis of all of the four energetically possible stereoisomers of 7-ethyl-2-methyl-1,6-dioxaspiro[4.5]decane

  摘要：

  DOI：

  10.1016/s0040-4020(01)91498-x

文献信息

• Efficient mercury-free preparation of vinyl and isopropenyl ethers of chiral secondary alcohols and α-hydroxyesters
  作者：Gilles Dujardin、Sandrine Rossignol、Eric Brown

  DOI：10.1016/0040-4039(95)00087-s

  日期：1995.3

  acetals 2a-h and 5a-d, readily deriving from the α-chiral alcohols 1a-h and ethyl vinyl ether or isopropenyl methyl ether, underwent selective elimination of primary alcohol upon treatment with triethylamine and trimethylsilyl trifluoromethanesulfonate, and thus afforded good to high yields of the chiral enol ethers 3a-h and 6a-d, respectively.

  易于从α-手性醇1a-h和乙基乙烯基醚或异丙烯基甲基醚衍生而来的混合缩醛2a-h和5a-d，在用三乙胺和三甲基甲硅烷基三氟甲磺酸酯处理后，选择性地除去了伯醇，因此得到了良好的高分别得到手性烯醇醚3a-h和6a-d的产率。
• Complementary diastereoselectivity in the intermolecular addition of titanium and magnesium naphtholates to asymmetric lactaldehydes
  作者：Robin G. F. Giles、Cynthia A. Joll、Melvyn V. Sargent、D. Matthew G. Tilbrook

  DOI：10.1039/a901456j

  日期：——

  S)-2-(1′-ethoxyethoxy)propanal 4 afforded solely (1S, 2R, 1″R or S)-1-(7′-benzyloxy-4′,5′-dimethoxy-1′-hydroxy-2′-naphthyl)-2-(1″-ethoxyethoxy)propan-1-ol 5, being the erythro product arising from anti addition. Complementary reaction of the naphthol 3 as its bromomagnesium naphtholate with aldehyde 4 gave rise solely to the alternative (1R, 2R, 1″R or S) diastereomer 6 . The naphthol 3 was prepared through the completely

  的7-苄氧基-4,5-二甲氧基-1-萘酚3作为其triisopropoxytitanium萘酚（2加成- [R，1' - [R或小号）-2-（1'-乙氧基乙氧基）丙醛4只得到（1小号，2 - [R，1“ R或S）-1-（7'-苄氧基-4'，5'-二甲氧基-1'-羟基-2'-萘基）-2-（1”-乙氧基乙氧基）丙-1-醇5，是反添加产生的赤字产物。萘酚3作为萘甲酸溴镁与醛4的互补反应仅产生了另一选择（1 R，2 R，1“ R或S）非对映体6。通过将2-甲氧基呋喃9完全区域选择性地加成到5-苄氧基-3-甲氧基脱氢苯8中来制备萘酚3。从香兰素中方便地制备了这种差异保护的双烷氧基苯并zy。
• Phosphane ligands with two binding sites of differing hardness for enantioselective Grignard cross coupling
  作者：Andreas Terfort、Henri Brunner

  DOI：10.1039/p19960001467

  日期：——

  A series of new, chiral phosphanes is presented, individual members of which were designed to serve as ligands in transition-metal mediated asymmetric Grignard cross coupling reactions. These ligands are characterized by a side chain containing one or two oxygen atoms with the capacity to act as binding sites for the incoming Grignard reagent. A number of structural parameters for the compounds was varied to learn about the reaction mechanism. Most of the ligands were tested in two cross coupling reactions, the formation of 3-phenylbut-1-ene and of 2,2′-dimethyl-1,1′-binaphthyl, respectively. Although both systems gave modest enantiomeric excesses it was not possible to make a comparison of their respective abilities.

  一系列新型手性膦被呈现出来，其中每个成员都被设计为在过渡金属介导的不对称Grignard交叉偶联反应中作为配体。这些配体的特点是具有含一个或两个氧原子的侧链，它们具备作为进入的Grignard试剂结合位点的能力。研究中改变了许多化合物的结构参数以深入了解反应机理。多数配体在两种交叉偶联反应中进行了测试，分别用于生成3-苯基丁-1-烯和2,2′-二甲基-1,1′-联萘。虽然这两个系统都获得了适度的对映体过量，但无法对其各自的能力进行比较。
• A novel synthesis of (3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-2-azetidinone, the versatile key intermediate of carbapenem synthesis, from (S)-ethyl lactate
  作者：Yoshio Ito、Takeo Kawabata、Shiro Terashima

  DOI：10.1016/s0040-4039(00)85317-4

  日期：——

  A highly efficient synthesis of the title compound was accomplished employing the addition of diketene to chiral imine as a key stereoselective reaction and using inexpensive ()-ethy1 lactate as a starting material.

  通过向手性亚胺中添加双烯酮作为关键的立体选择性反应，并使用廉价的（- ）-乳酸乙酯作为起始原料，可以实现标题化合物的高效合成。
• A New Synthesis of 3-Amino-2-alkenoates. Novel Synthetic Route to Amino Sugars<i>N</i>-Benzoyl-L-daunosamine and -L-acosamine
  作者：Tamejiro Hiyama、Kazuhiro Kobayashi、Kiyoharu Nishide

  DOI：10.1246/bcsj.60.2127

  日期：1987.6

  Alkanoate esters are found to couple with various nitriles to give (Z)-3-amino-2-alkenoates in good yields with the aid of a magnesium amide prepared by the reaction of ethylmagnesium bromide and diisopropylamine. The C–C bond forming reaction was applied to (2S,3S)-2,3-(cyclohexylidenedioxy)butanenitrile and the resulting adduct was successfully converted into N-benzoyl-L-daunosamine in 41% overall

  发现链烷酸酯在乙基溴化镁和二异丙胺反应制备的氨基镁的帮助下与各种腈偶联，以良好的产率得到(Z)-3-氨基-2-链烯酸酯。将 C-C 键形成反应应用于 (2S,3S)-2,3-(环己基二氧基) 丁腈，所得加合物通过一系列官能团成功转化为 N-苯甲酰基-L-道诺胺，总产率为 41%操纵；乙酰化、氢化、水解和苯甲酰化、内酯化和最终还原。通过类似的过程，(2R,3S)-2,3-(环己叉二氧基)丁腈以25%的总产率转化为N-苯甲酰基-L-acosamine。