(-)-methyl (2R,3R)-3-cyclohexyl-3-hydroxy-2-methylpropionate | 78604-73-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (-)-methyl (2R,3R)-3-cyclohexyl-3-hydroxy-2-methylpropionate
• 英文别名: (-)-threo-methyl 2-methyl-3-hydroxy-3-cyclohexylpropionate；methyl 3-cyclohexyl-3-hydroxy-2-methylpropanoate；methyl (2R,3R)-3-cyclohexyl-3-hydroxy-2-methylpropanoate
• CAS: 78604-73-6
• 化学式: C₁₁H₂₀O₃
• 分子量: 200.278
• InChiKey: OHADOFDGPAGHOA-SCZZXKLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙烯基乙醚 、 (-)-methyl (2R,3R)-3-cyclohexyl-3-hydroxy-2-methylpropionate 、 氢化铝锂 以72%的产率得到
  参考文献：
  名称：

  HOFSTRAAT, ROB G.;LANGE, JOS;SCHEEREN, HANS W.;NIVARD, RUTGER J. F., J. CHEM. SOC. PERKIN TRANS. PT I,(1988) N 8, C. 2315-2322

  摘要：

  DOI：
• 作为产物：
  描述：

  (+/-)-3-(tert-butyldimethylsilyloxy)-3-cyclohexyl-2-methyl-1-propene 在 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 草酰氯 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 双氧水 、 对甲苯磺酸 、 silver nitrate 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 58.67h， 生成 (-)-methyl (2R,3R)-3-cyclohexyl-3-hydroxy-2-methylpropionate
  参考文献：
  名称：

  Stereoselective acetalization of 1,3-alkanediols by l-menthone: application to the resolution of racemic 1,3-alkanediols and to the determination of the absolute configuration of enantiomeric 1,3-alkanediols

  摘要：

  A general and reliable method for the resolution of racemic 1,3-alkanediols, which involves their conversion into diastereomeric spiroacetals derived from l-menthone, is described. Thus, the reaction of the bis-O-trimethylsilyl derivatives of racemic 1,3-alkanediols with l-menthone in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate affords the diastereomeric spiroacetals 3 and 4. The two can be readily separated by silica gel column chromatography. Hydrolysis of each diastereomer under acidic conditions liberates the corresponding enantiomerically pure diol. An empirically derived correlation of configuration and H-1 NMR chemical shifts for spiroacetals 3 and 4 has been developed which is rationalized based on long-range effects due to the magnetic anisotropy inherent to the menthane ring in a rigid spiroacetal conformation. The method described here should be widely applicable to the determination of the absolute configuration of various 1,3-alkanediols.

  DOI：

  10.1021/jo00031a019

文献信息

• Stereoselectivity in the aldol reaction
  作者：A.I. Meyers、Yukio Yamamoto

  DOI：10.1016/0040-4020(84)80014-9

  日期：1984.1

  Chiral oxazolines, as their boron enolates derived from various boron triflates, react with aldehydes to give erythro-selectivity (97% + %) with enantiomeric purities of 50–60%. Achiral oxazolines as their boron enolates derived from diisopinocampheylborane give, on reaction with aldehydes, β-hydroxy esters with high threo-selectivity (90+%) in 77–85% ee. A variety of structurally different oxazolines

  手性恶唑啉是源自三氟甲磺酸三氟硼烷的硼烯酸酯，它与醛反应生成对映异构体纯度为50-60％的赤型选择性（97％+％）。非手性恶唑啉作为二异硫代樟脑硼烷的硼烯酸酯，与醛反应后，在77–85％ee中具有高苏式选择性（90％以上）的β-羟基酯。还研究了各种结构不同的恶唑啉，其中许多显示出高的赤型选择性。
• Synthesis and absolute configuration of optically active E-1-alkoxymethoxy-but-2-eny(tri-n-butyl)stannanes: stereoselective reactions with aldehydes
  作者：Vincent J. Jephcote、Andrew J. Pratt、Eric J. Thomas

  DOI：10.1039/c39840000800

  日期：——

  (1R)- and (1S)-1-[(–)-menthoxymethoxy]-E-but-2-enyl(tri-n-butyl)stannanes(5) and (6), whose configurations at C(1) were assigned by correlation with (2R)-and (2S)-pentan-2-ol, react stereoselectively on heating with benzaldeyde to give (3S,4R)- and (3R, 4R)-4hydroxy-3-methyl-cis-1,2-enol ethers (11) and (13), respectively.

  （1 R）-和（1 S）-1-[（-）-薄荷氧基甲氧基] -E -but-2-enyl（tri-n-butyl）stantanes（5）和（6），其构型在C（1 ）通过与（2 R）-和（2 S）-戊烷-2-醇的相关性分配，在加热后与苯并甲醛基立体反应，得到（3 S，4 R）-和（3 R，4 R）-4羟基3-甲基-顺式-1,2-烯醇醚（11）和（13）。
• Copper-ClickFerrophos-Complex-Catalyzed Enantioselective Reductive Aldol Reaction
  作者：Shin-ichi Fukuzawa、Minoru Kato、Hiroshi Oki、Kenichi Ogata

  DOI：10.1055/s-0029-1216724

  日期：——

  ClickFerrophos families and tested for the Cu(I)-catalyzed asymmetric reductive aldol reaction of ketones and aldehydes with an acrylic ester in the presence of phenylsilane. The Cu(I)-ClickFerrophos complex is efficient for the reaction of ketones with methyl acrylate to afford the erythro adducts both highly diastereo- and enantioselectively; the diastereomeric ratio of erythrolthreo is improved when compared

  我们已经制备了几个 ClickFerrophos 家族，并在苯基硅烷的存在下测试了酮和醛与丙烯酸酯的 Cu(I) 催化的不对称还原醛醇反应。Cu(I)-ClickFerrophos 配合物对于酮与丙烯酸甲酯的反应是有效的，以提供高度非对映选择性和对映选择性的赤型加合物；与类似的 Taniaphos 相比，erythrolthreo 的非对映体比例得到改善。
• Direct, enantioselective aldol coupling of aldehydes using chiral organic catalysts
  申请人：MacMillan W.C. David

  公开号：US20050197498A1

  公开（公告）日：2005-09-08

  Nonmetallic, chiral organic catalysts are used to catalyze an enantioselective aldol coupling reaction between aldehyde substrates. The reaction may be carried out with a single enolizable aldehyde, resulting in dimerization to give a β-hydroxy aldehyde, or trimerization to give a dihydroxy tetrahydropyran. The reaction may also conducted with an enolizable aldehyde and a second aldehyde, which may or may not be enolizable, so that the coupling is a cross-aldol reaction in which the α-carbon of the enolizable aldehyde adds to the carbonyl carbon of the second aldehyde in an enantioselective fashion. Reaction systems composed of at least one enolizable aldehyde, an optional additional aldehyde, and the nonmetallic chiral organic catalyst are also provided, as are methods of implementing the enantioselective aldol reaction in the synthesis of sugars.

  使用非金属手性有机催化剂催化醛底物的对映选择性Aldol偶联反应。该反应可以使用单个可烯化醛进行，产生二聚体以得到β-羟基醛，或三聚体以得到二羟基四氢吡喃。该反应也可以使用可烯化醛和第二个醛一起进行，第二个醛可以是可烯化的或不可烯化的，使偶联反应成为交叉Aldol反应，其中可烯化醛的α-碳以对映选择性的方式加到第二个醛的羰基碳上。还提供了由至少一个可烯化醛、一个可选的额外醛和非金属手性有机催化剂组成的反应系统，以及在糖的合成中实施对映选择性Aldol反应的方法。
• Enantioselective aldol reactions with high threo or erythro selectivity using boron azaenolates
  作者：A. I. Meyers、Yukio Yamamoto

  DOI：10.1021/ja00404a064

  日期：1981.7