(4R,5R)-5-Ethyl-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde | 133695-35-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R)-5-Ethyl-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde
• 英文别名: D-erythro-Pentose, 4,5-dideoxy-2,3-O-(1-methylethylidene)-(9CI)；(4R,5R)-5-ethyl-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
• CAS: 133695-35-9
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: SQANMADRLWWSPY-RQJHMYQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R)-4-[(E,1R,2R)-5-bromo-2-methyl-1-phenylmethoxypent-3-enyl]-2,2-dimethyl-1,3-dioxolane 、 (4R,5R)-5-Ethyl-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde 在 chromium chloride 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 以40%的产率得到(2R,3R,4R,5R/S,6R/S,7S,8R)-1,2:7,8-di-O-isopropylidene-4-methyl-5-vinyldecane-1,2,3,6,7,8-hexol
  参考文献：
  名称：

  高度 Felkin-Anh 选择性 Hiyama 向醛中添加手性烯丙基溴。在第一次合成肾霉酸及其对映体中的应用

  摘要：

  铬（II）介导的手性烯丙基溴与非手性和手性醛的加成（«Hiyama 反应»）相对于溴化物中 Cγ 的立体中心具有高 Felkin-Anh 选择性（表 II）。通过双立体分化实验（表III/IV）表明溴化物是添加物中的立体支配组分。该方法用于首次合成在地衣属 nephromopsis stracheyi 中发现的肾苔藓酸 (-) 及其对映异构体

  DOI：

  10.1021/ja00011a025

文献信息

• A mechanistic study of the Hiyama–Nozaki allylation: evidence for radical intermediates
  作者：Johann Mulzer、Achim R. Strecker、Lars Kattner

  DOI：10.1016/j.tetlet.2004.09.179

  日期：2004.11

  In course of chromium(II) mediated additions of relatively complex allylic bromides to aldehydes (Hiyama–Nozaki allylation) radical intermediates have been observed. From these findings a new mechanism of the allylation is derived.

  在铬（II）介导的过程中，已观察到相对复杂的烯丙基溴化物向醛（Hiyama–Nozaki烯丙基化）自由基中间体的添加。从这些发现中得出了烯丙基化的新机制。
• MULZER, JOHANN;KATTNER, LARS;STRECKER, ACHIM R.;SCHRODER, CHRISTIAN;BUSCH+, J. AMER. CHEM. SOC., 113,(1991) N1, C. 4218-4229
  作者：MULZER, JOHANN、KATTNER, LARS、STRECKER, ACHIM R.、SCHRODER, CHRISTIAN、BUSCH+

  DOI：——

  日期：——
• Glycolipid Derivative and Drug Containing the Same as Active Component
  申请人：Miyake Sachiko

  公开号：US20090227781A1

  公开（公告）日：2009-09-10

  Glycolipid derivatives having the formula (I): wherein R 1 indicates an aldopyranose residue, R 2 indicates a hydrogen atom or hydroxyl group, A indicates —CH 2 —, —CH(OH)—CH 2 — or —CH═CHCH 2 —, Z indicates —O— or —CH 2 —, when Z is —O— and x is an integer of 4 to 16, y indicates an integer of 26 to 35, when Z is —O— and x indicates an integer of 17 to 25, y indicates an integer of 0 to 35, when Z is —CH 2 — and x indicates an integer of 4 to 15, y indicates an integer of 26 to 35, and when Z is —CH 2 — and x indicates an integer of 16 to 25, y indicates an integer of 0 to 35 and a drug containing the glycolipid derivative for treatment of autoimmune arthritis and other autoimmune disease, bronchial asthma and other allergic diseases or diseases in which NKT cells or stimulation of NKT cells is known to be participating in the deterioration of conditions.
• Highly Felkin-Anh selective Hiyama additions of chiral allylic bromides to aldehydes. Application to the first synthesis of nephromopsinic acid and its enantiomer
  作者：Johann Mulzer、Lars Kattner、Achim R. Strecker、Christian Schroeder、Juergen Buschmann、Christian Lehmann、Peter Luger

  DOI：10.1021/ja00011a025

  日期：1991.5

  The chromium(II)-mediated addition («Hiyama reaction») of the chiral allylic bromides to achiral and chiral aldehydes proceeds with high Felkin-Anh selectivity with respect to the stereocenter at Cγ in the bromide (Table II). By double stereodifferentiation experiments (Tables III/IV) it was shown that the bromide is the stereodominating component in the addition. The methodology was applied to the

  铬（II）介导的手性烯丙基溴与非手性和手性醛的加成（«Hiyama 反应»）相对于溴化物中 Cγ 的立体中心具有高 Felkin-Anh 选择性（表 II）。通过双立体分化实验（表III/IV）表明溴化物是添加物中的立体支配组分。该方法用于首次合成在地衣属 nephromopsis stracheyi 中发现的肾苔藓酸 (-) 及其对映异构体