7-iodohept-6-en-1-ol | 244168-11-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 7-iodohept-6-en-1-ol
• CAS: 244168-11-4
• 化学式: C₇H₁₃IO
• 分子量: 240.084
• InChiKey: YEFWKXYHHZJIKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7-iodohept-6-en-1-ol 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到7-bromo-1-iodohept-1-ene
  参考文献：
  名称：

  The First Synthesis of Tonkinecin, an Annonaceous Acetogenin with a C-5 Carbinol Center

  摘要：

  [GRAPHICS]Reported herein is the first synthetic approach to tonkinecin (1) which uses a palladium catalyzed cross-coupling reaction between the tetrahydrofuran unit (4) and the butenolide (3) as the key step for constructing the backbone of 1, The stereogenic centers at C-5, C-21, C-22, and C-36 were derived from D-xylose, D-glucose, and L-lactate, respectively, whereas those at C-17, and C-18 were generated using Sharpless asymmetric dihydroxylation.

  DOI：

  10.1021/ol990062y
• 作为产物：
  描述：

  2H-吡喃,2-(6-庚炔-1-氧基)四氢 在 偶氮二异丁腈 、 三正丁基氢锡 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 生成 7-iodohept-6-en-1-ol
  参考文献：
  名称：

  The First Synthesis of Tonkinecin, an Annonaceous Acetogenin with a C-5 Carbinol Center

  摘要：

  [GRAPHICS]Reported herein is the first synthetic approach to tonkinecin (1) which uses a palladium catalyzed cross-coupling reaction between the tetrahydrofuran unit (4) and the butenolide (3) as the key step for constructing the backbone of 1, The stereogenic centers at C-5, C-21, C-22, and C-36 were derived from D-xylose, D-glucose, and L-lactate, respectively, whereas those at C-17, and C-18 were generated using Sharpless asymmetric dihydroxylation.

  DOI：

  10.1021/ol990062y

文献信息

• Enantioselective Syntheses of Monotetrahydrofuran Annonaceous Acetogenins Tonkinecin and Annonacin Starting from Carbohydrates
  作者：Tai-Shan Hu、Qian Yu、Yu-Lin Wu、Yikang Wu

  DOI：10.1021/jo005643b

  日期：2001.2.1

  The total synthesis of two mono-THF acetogenins, tonkinecin (1) and annonacin (2), is reported in full detail. Terminal acetylene 3 prepared from D-glucono-delta-lactone and asymmetric dihydroxylation was employed as a common intermediate for both targets 1 and 2. Pd(0)-catalyzed coupling reaction of 3 with vinyl iodides 4 and 5, the chiral centers of which were taken from D-xylose and S-(-)-ethyl

  详细报道了两种单-THF产乙酸素，唐宁霉素（1）和番农苷（2）的总合成。由D-葡萄糖酸-δ-内酯和不对称二羟基化反应制得的末端乙炔3被用作靶1和2的通用中间体。Pd（0）催化3与乙烯基碘4和5的偶联反应，其手性中心分别从D-木糖和S-（-）-乙基乳酸中提取，分别得到烯炔26和27。用二酰亚胺对26或27进行选择性氢化，然后除去MOM醚，从而完成了1的合成。在三氟化硼醚化物的存在下，3的锂衍生物与环氧化物6之间的偶联反应得到42。在环氧化物6中获得了两个手性中心来自L-抗坏血酸。随后的催化加氢和MOM保护得到43b。
• A concise formal total synthesis of lactimidomycin
  作者：Wei Li、Gunda I. Georg

  DOI：10.1039/c5cc02571k

  日期：——

  An ene–yne coupling/alkyne reduction tandem ring-closing reaction was employed for the formal total synthesis of the anti-tumor natural product lactimidomycin.

  一种烯-炔偶联/炔还原串联环合反应被用于合成抗肿瘤天然产物lactimidomycin的形式全合成。