racemic trans-2-phenylcyclohexyl glyoxylate | 98779-11-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: racemic trans-2-phenylcyclohexyl glyoxylate
• 英文别名: (-)-trans-2-phenylcyclohexylglyoxylate；trans-2-phenylcyclohexyl glyoxylate；Glyoxylic acid (1S)-2beta-phenylcyclohexane-1alpha-yl ester；[(1S,2R)-2-phenylcyclohexyl] 2-oxoacetate
• CAS: 98779-11-4
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: HMVRIQKKPOPFET-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  racemic trans-2-phenylcyclohexyl glyoxylate 在 咪唑 、 四氯化锡 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成
  参考文献：
  名称：

  紫杉醇A环系统的新合成。

  摘要：

  光学活性紫杉醇A-环单元3由2-异丙基-2-丙烯醇以11个步骤合成。立体异构中心通过不对称乙醛酸-烯反应和Sharpless不对称环氧化反应引入。

  DOI：

  10.1016/s0040-4020(01)86347-x
• 作为产物：
  描述：

  Acetic acid, (nitrooxy)-, 2-phenylcyclohexyl ester, trans- 在 sodium acetate 、 二甲基亚砜 作用下， 反应 1.0h， 以70%的产率得到racemic trans-2-phenylcyclohexyl glyoxylate
  参考文献：
  名称：

  Auxiliary structure and asymmetric induction in the ene reactions of chiral glyoxylates

  摘要：

  DOI：

  10.1021/jo00375a006

文献信息

• Synthesis of optically active 4-hydroxymandelic acid and derivatives via Regio- and Stereoselective Friedel-Crafts alkylation.
  作者：Franca Bigi、Giovanni Sartori、Raimondo Maggi、Edo Cantarelli、Gianni Galaverna

  DOI：10.1016/s0957-4166(00)82212-0

  日期：1993.1

  Optically active 4-hydroxymandelic esters were prepared in good yields and very high diastereoselectivity (up to 96% d.e.) viapara-hydroxyalkylation of phenolic ethers. Enantiomeric pure 4-hydroxymandelic acid is available by hydrolysis.

  通过酚醚的对羟基烷基化，以高收率和非常高的非对映选择性（高达96％de）制备旋光的4-羟基扁桃酸酯。对映体纯的4-羟基扁桃酸可通过水解获得。
• Total Synthesis of (−)-Heptemerone B and (−)-Guanacastepene E
  作者：Aubry K. Miller、Chambers C. Hughes、Joshua J. Kennedy-Smith、Stefan N. Gradl、Dirk Trauner

  DOI：10.1021/ja0660507

  日期：2006.12.1

  stereoselective, and convergent total synthesis of the unnatural enantiomer of the neodolastane diterpenoid heptemerone B has been completed. Saponification of (-)-heptemerone afforded (-)-guanacastepene E. The absolute stereochemistry of (-)-heptemerone B was thus established as 5-(S), the same as (-)-guanacastepene E. The longest linear sequence of the synthesis comprises 17 (18) steps from simple

  新多拉烷二萜类庚烯酮 B 的非天然对映异构体的简洁、立体选择性和收敛全合成已经完成。(-)-庚烯酮皂化得到(-)-胍那卡司汀E。因此，(-)-庚烯酮B的绝对立体化学确定为5-(S)，与(-)-胍那卡司酮E相同。最长的线性序列为该合成包括从简单的已知起始材料开始的 17 (18) 个步骤。我们的一般合成方法整合了一系列不同的反应，包括分子内 Heck 反应以创建一个四元立体中心和一个铜酸盐共轭添加以建立另一个。中央七元环通过不常见的电化学氧化闭合，而五元环通过闭环复分解形成。
• Efficient Asymmetric Synthesis of an A‐Ring Synthon for Pd‐Catalyzed Preparation of 1α‐Hydroxyvitamin D Metabolites and Analogs
  作者：Julian Loureiro、Lars Kattner、Antonio Mouriño

  DOI：10.1002/ejoc.202200314

  日期：2022.9.6

  An efficient Lewis acid-assisted asymmetric carbonyl-ene reaction to set the 1α-hydroxyl functionality of enol-triflate, precursor of the A-ring of the hormone calcitriol and its 1α-hydroxyderivatives, is described.

  描述了一种有效的路易斯酸辅助不对称羰基-烯反应来设置烯醇-三氟甲磺酸酯的 1α-羟基官能团，这是激素骨化三醇及其 1α-羟基衍生物的 A 环的前体。
• Stereoselective Synthesis of <i>meso</i>-2,6-Diaminopimelic Acid and Its Selectively Protected Derivatives
  作者：Yong Gao、Patricia Lane-Bell、John C. Vederas

  DOI：10.1021/jo972133h

  日期：1998.4.1

  Four synthetic routes to selectively protected derivatives and isomers of meso-diaminopimelic acid (DAP) (1a), a key constituent of bacterial peptidoglycan, were investigated. N-(tert-butyloxycarbonyl)-D-allylglycine (2) and N-(benzyloxycarbonyl)-L-allylglycine (4) were esterified to ethylene glycol and cyclized via olefin metathesis to a protected derivative 7 of 2,7-diaminosuberic acid. Analogous linking of propane-1,3-diol with 2 and potential precursors of N-(benzyloxycarbonyl)-L-vinylglycine moieties, such as N-(benzyloxycarbonyl)-L-glutamate or N-(benzyloxycarbonyl)-L-methionine sulfoxide, gave 12 or 15, both of which produced the alpha,beta-unsaturated ester 14 upon attempted generation of the vinylglycine precursor for olefin metathesis to DAP derivatives. An alternative route, based on SnCl4-catalyzed ene reaction of methyl N-(benzyloxycarbonyl)-L-allylglycinate (18) with glyoxylate esters of phenylcyclohexanol isomers as chiral auxiliaries, gave ca. 85:15 ratios of diastereomeric alcohols (19 or 20). These could be transformed to DAP derivatives in a series of steps employing azide displacement of corresponding mesylates to introduce the second nitrogen. A third method, involving reduction of pure dimethyl (6S)-2-keto-6-[N-(benzyloxycarbonyl)amino]pimelate (32) to the corresponding alcohol 33 with (S)-binaphthol-ruthenium catalyst as the key step, gives a 79:21 isomeric ratio. The fourth route employs the bis(oxazoline)-copper complex 41 as a chiral catalyst for the ene reaction of methyl (S)-4-(phenylthio)allylglycinate (39) and methyl glyoxylate to afford 42 in 94:6 isomeric ratio. Nickel boride removal of sulfur and the double bond in the presence of the Cbz group gives the desired alcohol, dimethyl (2S,6S)-6-[N(benzyloxycarbonyl)amino]-2-hydroxyheptane-1,7-dioate (33). The required selectively protected second nitrogen is introduced using Mitsunobu inversion with N-tert-butyl [[2-(trimethylsilyl)ethyl]sulfonyl]carbamate (34) as a key step.
• WHITESELL, J. K.;HWANG-HSING, CHEN;LAWRENCE, R. M., J. ORG. CHEM., 1985, 50, N 23, 4663-4664
  作者：WHITESELL, J. K.、HWANG-HSING, CHEN、LAWRENCE, R. M.

  DOI：——

  日期：——