(3R)-3-phenylmethoxyoxolan-2-ol | 1384132-55-1

• 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: (3R)-3-phenylmethoxyoxolan-2-ol
• CAS: 1384132-55-1
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: NPFVMZQFFFWAKY-NFJWQWPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R)-3-phenylmethoxyoxolan-2-ol 在 正丁基锂 、 四丁基氟化铵 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (R)-3-(benzyloxy)pent-4-yn-1-ol
  参考文献：
  名称：

  Modular and Stereoselective Synthesis of Tetrasubstituted Helical Alkenes via a Palladium-Catalyzed Domino Reaction

  摘要：

  A highly modular and stereoselective synthesis of tetrasubstituted helical alkenes is accomplished by a Pd-catalyzed norbornene-mediated domino reaction. This protocol features the rapid assembly of four C-C bonds via sequential C-H activations and carbopalladations along with efficient access to enantiopure bromoalkyl aryl alkyne precursors using homologative alkynylation as the key transformation. Three distinct elements of stereoselectivity were observed in the preparation of the chiral helical alkenes: retention of stereochemistry of the substrates, induced helical diastereoselectivity in the alkene formation, and the exclusive exo-facial selectivity of the norbornene incorporation.

  DOI：

  10.1021/ol301495q
• 作为产物：
  描述：

  (R)-α-benzyloxy-γ-butyrolactone 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (3R)-3-phenylmethoxyoxolan-2-ol
  参考文献：
  名称：

  Modular and Stereoselective Synthesis of Tetrasubstituted Helical Alkenes via a Palladium-Catalyzed Domino Reaction

  摘要：

  A highly modular and stereoselective synthesis of tetrasubstituted helical alkenes is accomplished by a Pd-catalyzed norbornene-mediated domino reaction. This protocol features the rapid assembly of four C-C bonds via sequential C-H activations and carbopalladations along with efficient access to enantiopure bromoalkyl aryl alkyne precursors using homologative alkynylation as the key transformation. Three distinct elements of stereoselectivity were observed in the preparation of the chiral helical alkenes: retention of stereochemistry of the substrates, induced helical diastereoselectivity in the alkene formation, and the exclusive exo-facial selectivity of the norbornene incorporation.

  DOI：

  10.1021/ol301495q

文献信息

• Highly Stereoselective Asymmetric Total Synthesis of (−)-Jimenezin via Sequential Intramolecular Amide Enolate Alkylation
  作者：Thien Nhan Lu、Minjung Kwak、Mallesham Samala、Minji Son、Jungjoong Hwang、Suresh Mandava、Thuy Trang Pham、Haeil Park、Hyoungsu Kim、Deukjoon Kim、Jongkook Lee

  DOI：10.1021/acs.orglett.2c00196

  日期：2022.3.4

  A highly stereoselective asymmetric total synthesis of (−)-jimenezin (1), a potent anticancer acetogenin, was efficiently completed with the key feature being a sequential intramolecular amide enolate alkylation (IAEA). Our investigation to probe the origin of the complete stereoselectivity in the second IAEA step to form the conformationally flexible tetrahydrofuran with perfect stereocontrol identified

  高效地完成了 (-)-jimenezin ( 1 ) 的高度立体选择性不对称全合成，这是一种有效的抗癌 acetogenin，其关键特征是顺序分子内酰胺烯醇化物烷基化 (IAEA)。我们在 IAEA 的第二步中探索完全立体选择性的起源以形成具有完美立体控制的构象灵活的四氢呋喃的研究确定了相邻四氢吡喃环中氧原子的存在是至关重要的。