2-((3a′R,3a1′S,9a′S)-5′-methoxy-2′,3a′,3a1′,9a′-tetrahydro-1′H-spiro[[1,3]dioxolane-2,3′-phenanthro[4,5-bcd]furan]-3a1′-yl)-acetaldehyde | 1426537-71-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 2-((3a′R,3a1′S,9a′S)-5′-methoxy-2′,3a′,3a1′,9a′-tetrahydro-1′H-spiro[[1,3]dioxolane-2,3′-phenanthro[4,5-bcd]furan]-3a1′-yl)-acetaldehyde
• 英文别名: 2-[(8'S,12'R,13'S)-2'-methoxyspiro[1,3-dioxolane-2,11'-15-oxatetracyclo[10.2.1.05,14.08,13]pentadeca-1,3,5(14),6-tetraene]-13'-yl]acetaldehyde
• CAS: 1426537-71-4
• 化学式: C₁₉H₂₀O₅
• 分子量: 328.365
• InChiKey: GNRZKVWPLPUELP-XWIAVFTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	2-((3a′R,3a1′S,9a′S)-5′-methoxy-2′,3a′,3a1′,9a′-tetrahydro-1′H-spiro[[1,3]dioxolane-2,3′-phenanthro[4,5-bcd]furan]-3a1′-yl)-N,N-dimethylethanamine	1426537-69-0	C21H27NO4	357.45
  ——	2-((3a′R,3a1′S,9a′S)-5′-methoxy-2′,3a′,3a1′,9a′-tetrahydro-1′H-spiro[[1,3]dioxolane-2,3′-phenanthro[4,5-bcd]furan]-3a1′-yl)-N,N-dimethylethanamine oxide	1426537-70-3	C21H27NO5	373.449
  ——	(-)-dihydrocodeinone ethyleneketal	10093-66-0	C20H25NO4	343.423
  二氢可待因酮	Hydrocodone	125-29-1	C18H21NO3	299.37

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	2-((3a′R,3a1′S,9a′S)-5′-methoxy-2′,3a′,3a1′,9a′-tetrahydro-1′H-spiro[[1,3]dioxolane-2,3′-phenanthro[4,5-bcd]furan]-3a1′-yl)-ethanethiol	1426537-76-9	C19H22O4S	346.447
  ——	(3a′R,3a1′S,9a′S)-3a1′-(2-chloroethyl)-5′-methoxy-2′,3a′,3a1′,9a′-tetrahydro-1′H-spiro[[1,3]dioxolane-2,3′-phenanthro[4,5-bcd]-furan]	1426537-84-9	C19H21ClO4	348.826
  ——	S-(2-((3a′R,3a1′S,9a′S)-5′-methoxy-2′,3a′,3a1′,9a′-tetrahydro-1′H-spiro[[1,3]dioxolane-2,3′-phenanthro[4,5-bcd]furan]-3a1′-yl)-ethyl) ethanethioate	1426537-75-8	C21H24O5S	388.485
  ——	2-((3a′R,3a1′S,9a′S)-5′-methoxy-2′,3a′,3a1′,9a′-tetrahydro-1′H-spiro[[1,3]dioxolane-2,3′-phenanthro[4,5-bcd]furan]-3a1′-yl)ethyl 4-methylbenzenesulfonate	1426537-74-7	C26H28O7S	484.57
  ——	ethyl (1,1-diethoxyethyl)(2-((3a′R,3a1′S,9a′S)-5′-methoxy-2′,3a′,3a1′,9a′-tetrahydro-1′H-spiro[[1,3]dioxolane-2,3′-phenanthro[4,5-bcd]furan]-3a1′-yl)ethyl)phosphinate	——	C27H39O8P	522.576
  ——	(4R,4aR,7aR,12bS)-9-methoxy-2,4,4a,5,6,7a-hexahydro-1H-spiro-[4,12-methanobenzofuro[3,2-e]isochromene-7,2′-[1,3]dioxolane]	1426537-72-5	C19H22O5	330.381
  ——	(4R,4aR,7aR,12bS)-9-methoxy-2,4,4a,5,6,7a-hexahydro-1H-spiro[4,12-methanoisothiochromeno[5,4a-b]-benzofuran-7,2′-[1,3]dioxolane]	1426537-77-0	C19H22O4S	346.447
  ——	(4R,4aR,7aR,12bS)-9-methoxy-1,2,4,4a,5,6-hexahydro-4,12-methanobenzofuro[3,2-e]isochromen-7(7aH)-one	1426537-73-6	C17H18O4	286.328
  ——	(4R,4aR,7aR,12bS)-9-methoxy-1,2,4,4a,5,6-hexahydro-4,12-methanoisothiochromeno[5,4a-b]benzofuran-7(7aH)-one	1426537-78-1	C17H18O3S	302.394
  ——	(4R,4aR,7aR,12bS)-9-methoxy-1,2,4,4a,5,6-hexahydro-4,12-methanoisothiochromeno[5,4a-b]benzofuran-7(7aH)-one 3,3-dioxide	1426537-79-2	C17H18O5S	334.393

反应信息

• 作为反应物：
  描述：

  2-((3a′R,3a1′S,9a′S)-5′-methoxy-2′,3a′,3a1′,9a′-tetrahydro-1′H-spiro[[1,3]dioxolane-2,3′-phenanthro[4,5-bcd]furan]-3a1′-yl)-acetaldehyde 在 吡啶 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 28.5h， 生成 S-(2-((3a′R,3a1′S,9a′S)-5′-methoxy-2′,3a′,3a1′,9a′-tetrahydro-1′H-spiro[[1,3]dioxolane-2,3′-phenanthro[4,5-bcd]furan]-3a1′-yl)-ethyl) ethanethioate
  参考文献：
  名称：

  Heteroatom Analogues of Hydrocodone: Synthesis and Biological Activity

  摘要：

  Heteroatom analogues of hydrocodone, in which the N-methyl functionality was replaced with oxygen, sulfur, sulfoxide, and sulfone, were prepared by a short sequence from the ethylene glycol ketal of hydrocodone; a carbocyclic analogue of bisnorhydrocodone was also prepared. The compounds were tested for receptor binding and revealed moderate levels of activity for the sulfone analogue of hydrocodone.

  DOI：

  10.1021/jo3026753
• 作为产物：
  描述：

  二氢可待因酮 在 三甲基氯硅烷 、 双氧水 、 三氟乙酸酐 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 72.5h， 生成 2-((3a′R,3a1′S,9a′S)-5′-methoxy-2′,3a′,3a1′,9a′-tetrahydro-1′H-spiro[[1,3]dioxolane-2,3′-phenanthro[4,5-bcd]furan]-3a1′-yl)-acetaldehyde
  参考文献：
  名称：

  Heteroatom Analogues of Hydrocodone: Synthesis and Biological Activity

  摘要：

  Heteroatom analogues of hydrocodone, in which the N-methyl functionality was replaced with oxygen, sulfur, sulfoxide, and sulfone, were prepared by a short sequence from the ethylene glycol ketal of hydrocodone; a carbocyclic analogue of bisnorhydrocodone was also prepared. The compounds were tested for receptor binding and revealed moderate levels of activity for the sulfone analogue of hydrocodone.

  DOI：

  10.1021/jo3026753

文献信息

• Heteroatom Analogues of Hydrocodone: Synthesis and Biological Activity
  作者：Robert D. Giacometti、Jan Duchek、Lukas Werner、Afeef S. Husni、Christopher R. McCurdy、Stephen J. Cutler、D. Phillip Cox、Tomas Hudlicky

  DOI：10.1021/jo3026753

  日期：2013.4.5

  Heteroatom analogues of hydrocodone, in which the N-methyl functionality was replaced with oxygen, sulfur, sulfoxide, and sulfone, were prepared by a short sequence from the ethylene glycol ketal of hydrocodone; a carbocyclic analogue of bisnorhydrocodone was also prepared. The compounds were tested for receptor binding and revealed moderate levels of activity for the sulfone analogue of hydrocodone.