(2R)-2-((3R,6S)-6-methyl-6-((E)-3-(2-methyl-5-oxotetrahydrofuran-2-yl)allyl)-1,2-dioxan-3-yl)propanoic acid | 1245046-41-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: (2R)-2-((3R,6S)-6-methyl-6-((E)-3-(2-methyl-5-oxotetrahydrofuran-2-yl)allyl)-1,2-dioxan-3-yl)propanoic acid
• 英文别名: negombatoperoxide C；Negombatoperoxide C/D；(2R)-2-[(3R,6S)-6-methyl-6-[(E)-3-(2-methyl-5-oxooxolan-2-yl)prop-2-enyl]dioxan-3-yl]propanoic acid
• CAS: 1245046-41-6
• 化学式: C₁₆H₂₄O₆
• 分子量: 312.363
• InChiKey: HAZACBAWFGKIBT-AGIJGJRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲醇 、 (2R)-2-((3R,6S)-6-methyl-6-((E)-3-(2-methyl-5-oxotetrahydrofuran-2-yl)allyl)-1,2-dioxan-3-yl)propanoic acid 在 4-二甲氨基吡啶 、 4-(dimethylamino)pyridine hydrochloride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以1.1 mg的产率得到methyl (2R)-2-[(3R,6S)-6-methyl-6-[(E)-3-(2-methyl-5-oxooxolan-2-yl)prop-2-enyl]dioxan-3-yl]propanoate
  参考文献：
  名称：

  Norterpenoids and Related Peroxides from the Formosan Marine Sponge Negombata corticata

  摘要：

  Six norterpenes including negombatoperoxides A and B (4 and 5), the inseparable epimers negombatoperoxides C and D (6 and 7), negombatodiol (8), and negombatolactone (9), in combination with three known compounds, (+)-nuapapuin B (1), (+)-nuapapuin B methyl ester (2), and (+)-aikupikoxide C (3), were isolated from the Formosan marine sponge Negombata corticata. In addition, 6,6-dimethylundecane-2,5,10-trione (10) was isolated for the first time from a natural source. Their structures, including relative configurations, were elucidated on the basis of interpretation of spectroscopic data and by the application of the empirical rule established by Capon and MacLeod. The absolute configurations of 8 and 9 were established by the application of Mosher's method and comparison of CD data with known lactones, respectively. Cytotoxicity of these isolates against human breast carcinoma, human liver carcinoma, and human lung carcinoma cell lines was evaluated.

  DOI：

  10.1021/np100353x
• 作为产物：
  描述：

  在 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 以60%的产率得到(2R)-2-((3R,6S)-6-methyl-6-((E)-3-(2-methyl-5-oxotetrahydrofuran-2-yl)allyl)-1,2-dioxan-3-yl)propanoic acid
  参考文献：
  名称：

  对映选择性合成Muqubilin和Negombatoperoxides B和C / D

  摘要：

  通过对映选择性路线合成了多巴胆碱，negombatoperoxide B和negombatoperoxide C / D，其四级中心衍生自已知绝对构型的过氧手性结构单元。通过不对称的羟醛缩合引入C-2 / C-3立体异构中心，并通过氢过氧化物与甲磺酸酯的分子内烷基化反应构建1,2-二恶烷环。合成样品显示的物理和光谱数据与文献报道的一致，因此验证了天然产物的构型。还简要探讨了这种环状过氧化物可能更快地对映体进入1,2-二恶烷-醛醇部分（C-1至C-6）的方法，其中C-2 / C-3立体异构中心是通过[ 2 + 2]环加法，而1

  DOI：

  10.1021/acs.joc.0c03040

文献信息

• Enantioselective Synthesis Muqubilin and Negombatoperoxides B and C/D
  作者：Xiao-Tao Wang、Yikang Wu

  DOI：10.1021/acs.joc.0c03040

  日期：2021.3.5

  Muqubilin, negombatoperoxide B, and negombatoperoxide C/D were synthesized through enantioselective routes, with the quaternary center derived from a peroxy chiral building block of known absolute configuration. The C-2/C-3 stereogenic centers were introduced by asymmetric aldol condensation, and the 1,2-dioxane ring was constructed via an intramolecular alkylation of a hydroperoxide with a mesylate

  通过对映选择性路线合成了多巴胆碱，negombatoperoxide B和negombatoperoxide C / D，其四级中心衍生自已知绝对构型的过氧手性结构单元。通过不对称的羟醛缩合引入C-2 / C-3立体异构中心，并通过氢过氧化物与甲磺酸酯的分子内烷基化反应构建1,2-二恶烷环。合成样品显示的物理和光谱数据与文献报道的一致，因此验证了天然产物的构型。还简要探讨了这种环状过氧化物可能更快地对映体进入1,2-二恶烷-醛醇部分（C-1至C-6）的方法，其中C-2 / C-3立体异构中心是通过[ 2 + 2]环加法，而1
• Norterpenoids and Related Peroxides from the Formosan Marine Sponge <i>Negombata corticata</i>
  作者：Chih-Hua Chao、Kuei-Ju Chou、Guey-Horng Wang、Yang-Chang Wu、Li-Hsueh Wang、Jeng-Ping Chen、Jyh-Horng Sheu、Ping-Jyun Sung

  DOI：10.1021/np100353x

  日期：2010.9.24

  Six norterpenes including negombatoperoxides A and B (4 and 5), the inseparable epimers negombatoperoxides C and D (6 and 7), negombatodiol (8), and negombatolactone (9), in combination with three known compounds, (+)-nuapapuin B (1), (+)-nuapapuin B methyl ester (2), and (+)-aikupikoxide C (3), were isolated from the Formosan marine sponge Negombata corticata. In addition, 6,6-dimethylundecane-2,5,10-trione (10) was isolated for the first time from a natural source. Their structures, including relative configurations, were elucidated on the basis of interpretation of spectroscopic data and by the application of the empirical rule established by Capon and MacLeod. The absolute configurations of 8 and 9 were established by the application of Mosher's method and comparison of CD data with known lactones, respectively. Cytotoxicity of these isolates against human breast carcinoma, human liver carcinoma, and human lung carcinoma cell lines was evaluated.