(1R)-1-<(2R)-1,4-dioxaspiro<4.5>dec-2-yl>ethanol | 108552-77-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R)-1-<(2R)-1,4-dioxaspiro<4.5>dec-2-yl>ethanol
• 英文别名: (2R,3R)-1,2-Cyclohexylidenebutane-1,2,3-triol；(R)-1-((R)-1,4-dioxaspiro[4.5]decan-2-yl)ethanol；(1R)-1-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]ethanol
• CAS: 108552-77-8
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: SASZOMPJCVAWQU-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (R)-1,4-二氧杂螺[4,5]癸烷-2-甲醛 在 chromium(VI) oxide 、 葡萄糖 、 potassium phosphate buffer pH 6 、 硫酸 、 magnesium 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 32.0h， 生成 (1R)-1-<(2R)-1,4-dioxaspiro<4.5>dec-2-yl>ethanol
  参考文献：
  名称：

  Schroetter, Eberhard; Luong, Tran Thanh; Schick, Hans, Journal fuer Praktische Chemie (Leipzig), 1991, vol. 333, # 6, p. 875 - 888

  摘要：

  DOI：

文献信息

• Metal-Dependent Reaction Tuning with Cyclopentylmetal Reagents: Application to the Asymmetric Synthesis of (+)-α-Conhydrine and (<i>S</i>)-2-Cyclopentyl-2-phenylglycolic Acid
  作者：Siddharth Roy、Anubha Sharma、Soumyaditya Mula、Subrata Chattopadhyay

  DOI：10.1002/chem.200801603

  日期：2009.2.2

  The reaction of halocyclopentane organometallic reagents can be tuned by the choice of metal (see scheme). Cyclopentylmagnesium bromide reduces aldehydes and ketones to the corresponding alcohols. However, in the presence of ZnCl2, normal Grignard addition to the ketones gives tertiary alcohols with complete diastereoselectivity. These protocols were used in the asymmetric synthesis of two medicinally

  调整：卤环戊烷有机金属试剂的反应可通过选择金属来调整（参见方案）。环戊基溴化镁将醛和酮还原为相应的醇。然而，在存在ZnCl 2的情况下，向酮中常规的格利雅（Grignard）加成会产生具有完全非对映选择性的叔醇。这些规程用于两种医学上重要的化合物的不对称合成。
• A general and concise stereodivergent chiral pool approach toward trans-(4S,5R)- and cis-(4R,5R)-5-alkyl-4-methyl-γ-butyrolactones: Syntheses of (+)-trans- and (+)-cis-whisky and cognac lactones from d-(+)-mannitol
  作者：Avrajit Manna、Ipsita Chakraborty、Sandip Chatterjee、Tanurima Bhaumik

  DOI：10.1016/j.carres.2021.108452

  日期：2021.12

  A straightforward synthesis of (+)-trans-(4S,5R)- and (+)-cis-(4R,5R)-whisky lactones starting from d-(+)-mannitol has been reported here in fewer number of efficient steps compared to existing literature processes involving d-mannitol as the chiral pool starting material. Chiron approach directly translated chirality of d-mannitol to one of the two chiral centers in these target molecules. Toward

  从d -(+)-甘露醇开始直接合成 (+)-反式-(4 S ,5 R )- 和 (+)-顺式-(4 R ,5 R )-威士忌内酯的报道较少与涉及d-甘露醇作为手性池起始材料的现有文献方法相比，有效步骤的数量。Chiron 方法直接将d-甘露醇的手性转化为这些靶分子中的两个手性中心之一。为此，立体异构纯的反式和顺式在倒数第二步中形成碘甲基-γ-内酯。这两种作为通用的高级通用中间体也分别转化为 (+)-反式-(4 S ,5 R )- 和 (+)-顺式-(4 R ,5 R )-干邑内酯。据我们所知，迄今为止还没有报道从d-甘露醇开始合成干邑内酯。所有这些内酯都被确定为陈年酒精饮料的关键香气成分。
• (R)-2,3-O-Cyclohexylideneglyceraldehyde, a Versatile Intermediate for Asymmetric Synthesis of Chiral Alcohol
  作者：A. Chattopadhyay、V. R. Mamdapur

  DOI：10.1021/jo00108a020

  日期：1995.2

  Grignard addition to (R)-2,3-O-cyclohexylideneglyceraldehyde (IIa) gave rise to column chromatographically separable diastereo alcohols 2 and 3 including highly functionalized and synthetically exploitable homoallylic alcohols 2e and 3e and homopropargylic alcohols 2f and 3f. Compound 3c on functional manipulation gave rise to (-)-coriolic acid synthon 6.
• Chattopadhyay A., Mamdapur V. R., J. Org. Chem, 60 (1995) N 3, S 585-587
  作者：Chattopadhyay A., Mamdapur V. R.

  DOI：——

  日期：——
• Schroetter, Eberhard; Luong, Tran Thanh; Schick, Hans, Journal fuer Praktische Chemie (Leipzig), 1991, vol. 333, # 6, p. 875 - 888
  作者：Schroetter, Eberhard、Luong, Tran Thanh、Schick, Hans

  DOI：——

  日期：——